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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:51:59 UTC

HMDB ID

HMDB0015442

Secondary Accession Numbers

HMDB15442

Metabolite Identification

Common Name

Butethal

Description

Butethal is only found in individuals that have used or taken this drug. It is a sedative and a hypnotic drug.Butethal binds at a distinct binding site associated with a Cl^- ionopore at the GABA_A receptor, increasing the duration of time for which the Cl^- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged. All of these effects are associated with marked decreases in GABA-sensitive neuronal calcium conductance (gCa). The net result of barbiturate action is acute potentiation of inhibitory GABAergic tone. Barbiturates also act through potent (if less well characterized) and direct inhibition of excitatory AMPA-type glutamate receptors, resulting in a profound suppression of glutamatergic neurotransmission.

Structure

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

HMDB0015442
     RDKit          3D
Butethal
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.9538    0.4798   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8431    1.5297   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0835    1.3855    1.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841    0.1115    1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152   -0.2885    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -1.6304    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070   -2.7463    0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709    0.6616    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638    0.8881    1.6591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    1.3048   -0.5799 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    1.0669   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7345    1.6603   -2.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    0.1815   -2.2017 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3863   -0.4695   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -1.2552   -1.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510    1.0180   -0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -0.2229    0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823   -0.0103   -1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386    1.4036   -1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214    2.5523   -0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    1.4930    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402    2.2872    1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657    0.1013    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1397   -0.7363    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081   -1.4895    1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.9174    0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778   -2.6289    1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -3.0907   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548   -3.6266    1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383    1.9787   -0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557    0.0085   -3.1916 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  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
  3 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

1353
  Mrv0541 02231215242D          

 15 15  0  0  0  0            999 V2000
    1.6500   -0.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.4290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.6665    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 14  2  0  0  0  0
  4 10  1  0  0  0  0
  4 14  1  0  0  0  0
  5 11  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 10  1  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 12  1  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015442

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCC1(CC)C(=O)NC(=O)NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H16N2O3/c1-3-5-6-10(4-2)7(13)11-9(15)12-8(10)14/h3-6H2,1-2H3,(H2,11,12,13,14,15)

> <INCHI_KEY>
STDBAQMTJLUMFW-UHFFFAOYSA-N

> <FORMULA>
C10H16N2O3

> <MOLECULAR_WEIGHT>
212.2456

> <EXACT_MASS>
212.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.615960524107212

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
1.606232150333333

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.154863311944384

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.484749988910163

> <JCHEM_POLAR_SURFACE_AREA>
75.27

> <JCHEM_REFRACTIVITY>
53.45429999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butethal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015442
     RDKit          3D
Butethal
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.9538    0.4798   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8431    1.5297   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0835    1.3855    1.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841    0.1115    1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152   -0.2885    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -1.6304    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070   -2.7463    0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709    0.6616    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638    0.8881    1.6591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    1.3048   -0.5799 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    1.0669   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7345    1.6603   -2.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    0.1815   -2.2017 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3863   -0.4695   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -1.2552   -1.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510    1.0180   -0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -0.2229    0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823   -0.0103   -1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386    1.4036   -1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214    2.5523   -0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    1.4930    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402    2.2872    1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657    0.1013    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1397   -0.7363    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081   -1.4895    1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.9174    0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778   -2.6289    1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -3.0907   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548   -3.6266    1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383    1.9787   -0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557    0.0085   -3.1916 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  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
  3 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: 1353                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       3.080  -0.357   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415  -0.357   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748  -4.977   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.414  -2.667   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.081  -2.667   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.748  -0.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.518   0.976   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.977   0.976   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081  -1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.518   3.644   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.437   0.976   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -3.437   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748   4.977   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   10   14                                                       
CONECT    5   11   14                                                       
CONECT    6    7    8   10   11                                             
CONECT    7    6    9                                                       
CONECT    8    6   13                                                       
CONECT    9    7   12                                                       
CONECT   10    1    4    6                                                  
CONECT   11    2    5    6                                                  
CONECT   12    9   15                                                       
CONECT   13    8                                                            
CONECT   14    3    4    5                                                  
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0015442
HETATM    1  C1  UNL     1       2.954   0.480  -0.349  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.843   1.530  -0.279  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.083   1.386   1.000  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.384   0.112   1.204  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.715  -0.288   0.300  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.278  -1.630   0.775  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.307  -2.746   0.794  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.871   0.662   0.488  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.264   0.888   1.659  1.00  0.00           O  
HETATM   10  N1  UNL     1      -2.529   1.305  -0.580  1.00  0.00           N  
HETATM   11  C9  UNL     1      -2.123   1.067  -1.914  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.735   1.660  -2.854  1.00  0.00           O  
HETATM   13  N2  UNL     1      -1.053   0.182  -2.202  1.00  0.00           N  
HETATM   14  C10 UNL     1      -0.386  -0.469  -1.123  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.553  -1.255  -1.486  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.951   1.018  -0.309  1.00  0.00           H  
HETATM   17  H2  UNL     1       2.942  -0.223   0.483  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.982  -0.010  -1.358  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.139   1.404  -1.120  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.321   2.552  -0.352  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.873   1.493   1.820  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.440   2.287   1.188  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.066   0.101   2.254  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.140  -0.736   1.201  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.708  -1.489   1.799  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.129  -1.917   0.129  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.578  -2.629   1.423  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.072  -3.091  -0.250  1.00  0.00           H  
HETATM   29  H14 UNL     1      -0.855  -3.627   1.269  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.338   1.979  -0.420  1.00  0.00           H  
HETATM   31  H16 UNL     1      -0.756   0.009  -3.192  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   19   20
CONECT    3    4   21   22
CONECT    4    5   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

HMDB0015442
     RDKit          3D
Butethal
 31 31  0  0  0  0  0  0  0  0999 V2000
    2.9538    0.4798   -0.3491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8431    1.5297   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0835    1.3855    1.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3841    0.1115    1.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7152   -0.2885    0.3001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2777   -1.6304    0.7749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3070   -2.7463    0.7944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8709    0.6616    0.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2638    0.8881    1.6591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5289    1.3048   -0.5799 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1234    1.0669   -1.9136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7345    1.6603   -2.8540 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0525    0.1815   -2.2017 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3863   -0.4695   -1.1228 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5532   -1.2552   -1.4857 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9510    1.0180   -0.3089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9418   -0.2229    0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9823   -0.0103   -1.3578 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1386    1.4036   -1.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3214    2.5523   -0.3520 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8733    1.4930    1.8197 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4402    2.2872    1.1880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0657    0.1013    2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1397   -0.7363    1.2009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7081   -1.4895    1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1288   -1.9174    0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5778   -2.6289    1.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0721   -3.0907   -0.2502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8548   -3.6266    1.2689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3383    1.9787   -0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557    0.0085   -3.1916 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  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
  3 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
Neonal	Kegg
5-Butyl-5-ethyl-2,4,6(1H,3H,5H)-pyrimidinetrione	HMDB
5-Butyl-5-ethylbarbituric acid	HMDB
5-Ethyl-5-butylbarbituric acid	HMDB
5-Ethyl-5-N-butylbarbituric acid	HMDB
Butabarbitol	HMDB
Butobarbital	HMDB
Butobarbitalum	HMDB
Butobarbitone	HMDB
Butobarbitural	HMDB
Butyl,5-ethylbarbituric acid	HMDB
Soneryl	HMDB
Butethal, monosodium salt	HMDB
Butobarbital, sodium salt	HMDB
Butethal	KEGG

Chemical Formula

C₁₀H₁₆N₂O₃

Average Molecular Weight

212.2456

Monoisotopic Molecular Weight

212.116092388

IUPAC Name

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

Traditional Name

butethal

CAS Registry Number

77-28-1

SMILES

CCCCC1(CC)C(=O)NC(=O)NC1=O

InChI Identifier

InChI=1S/C10H16N2O3/c1-3-5-6-10(4-2)7(13)11-9(15)12-8(10)14/h3-6H2,1-2H3,(H2,11,12,13,14,15)

InChI Key

STDBAQMTJLUMFW-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Barbituric acid derivatives

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015442)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	128.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.27 g/L	Not Available
LogP	1.73	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.27 g/L	ALOGPS
logP	1.65	ALOGPS
logP	1.61	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	4	ChemAxon
Refractivity	53.45 m³·mol⁻¹	ChemAxon
Polarizability	21.62 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]+	150.032	31661259
DarkChem	[M-H]-	145.884	31661259
DeepCCS	[M+H]+	148.57	30932474
DeepCCS	[M-H]-	144.741	30932474
DeepCCS	[M-2H]-	182.215	30932474
DeepCCS	[M+Na]+	157.755	30932474
AllCCS	[M+H]+	148.6	32859911
AllCCS	[M+H-H2O]+	144.6	32859911
AllCCS	[M+NH4]+	152.2	32859911
AllCCS	[M+Na]+	153.3	32859911
AllCCS	[M-H]-	150.0	32859911
AllCCS	[M+Na-2H]-	150.6	32859911
AllCCS	[M+HCOO]-	151.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Butethal	CCCCC1(CC)C(=O)NC(=O)NC1=O	3157.7	Standard polar	33892256
Butethal	CCCCC1(CC)C(=O)NC(=O)NC1=O	1652.4	Standard non polar	33892256
Butethal	CCCCC1(CC)C(=O)NC(=O)NC1=O	1640.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Butethal,1TMS,isomer #1	CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1684.1	Semi standard non polar	33892256
Butethal,1TMS,isomer #1	CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1829.4	Standard non polar	33892256
Butethal,1TMS,isomer #1	CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2806.2	Standard polar	33892256
Butethal,2TMS,isomer #1	CCCCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1666.7	Semi standard non polar	33892256
Butethal,2TMS,isomer #1	CCCCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1878.4	Standard non polar	33892256
Butethal,2TMS,isomer #1	CCCCC1(CC)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2296.0	Standard polar	33892256
Butethal,1TBDMS,isomer #1	CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1897.4	Semi standard non polar	33892256
Butethal,1TBDMS,isomer #1	CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2063.7	Standard non polar	33892256
Butethal,1TBDMS,isomer #1	CCCCC1(CC)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2843.3	Standard polar	33892256
Butethal,2TBDMS,isomer #1	CCCCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2091.5	Semi standard non polar	33892256
Butethal,2TBDMS,isomer #1	CCCCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2321.0	Standard non polar	33892256
Butethal,2TBDMS,isomer #1	CCCCC1(CC)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2434.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Butethal EI-B (Non-derivatized)	splash10-0006-9600000000-eef99ddbb9fc48cf8ed4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butethal CI-B (Non-derivatized)	splash10-03di-0090000000-3021b7118b324b8467bd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butethal EI-B (Non-derivatized)	splash10-0006-9600000000-eef99ddbb9fc48cf8ed4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Butethal CI-B (Non-derivatized)	splash10-03di-0090000000-3021b7118b324b8467bd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butethal GC-MS (Non-derivatized) - 70eV, Positive	splash10-05ru-8900000000-4af4f13ca7ae2bc7fcda	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Butethal GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 10V, Positive-QTOF	splash10-03di-1390000000-43ecd68f229c3c3bc90c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 20V, Positive-QTOF	splash10-0006-4900000000-1b15cbf105e1de888220	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 40V, Positive-QTOF	splash10-052f-9000000000-205e856802a03c319f4c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 10V, Negative-QTOF	splash10-0296-7940000000-170e8b066d6c58e18ace	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 20V, Negative-QTOF	splash10-0006-9500000000-aa05ed5e0280f5ac92f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 40V, Negative-QTOF	splash10-0006-9500000000-8169dd5585539f0b6ae0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 10V, Positive-QTOF	splash10-0a4i-0920000000-404a31fe18ef594f21df	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 20V, Positive-QTOF	splash10-0a4j-3900000000-e48f90bfca377565c24e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 40V, Positive-QTOF	splash10-0002-9400000000-f5a557249efe744106d5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 10V, Negative-QTOF	splash10-03di-0090000000-39954a7265a9cf3de21b	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 20V, Negative-QTOF	splash10-03dl-6090000000-1346133bfd2e9697f150	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Butethal 40V, Negative-QTOF	splash10-0006-9300000000-b5bed8f717a537bd2583	2021-10-11	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 DB01353	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01353	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

DB01353

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6229

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Butobarbital

METLIN ID

Not Available

PubChem Compound

6473

PDB ID

Not Available

ChEBI ID

519412

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 ]
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 ]
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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

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 Butethal (HMDB0015442)

MOL for HMDB0015442 (Butethal)

3D MOL for HMDB0015442 (Butethal)

3D SDF for HMDB0015442 (Butethal)

3D-SDF for HMDB0015442 (Butethal)

PDB for HMDB0015442 (Butethal)

3D PDB for HMDB0015442 (Butethal)

SMILES for HMDB0015442 (Butethal)

INCHI for HMDB0015442 (Butethal)

Structure for HMDB0015442 (Butethal)

3D Structure for HMDB0015442 (Butethal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References

References

References

References

References