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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:55 UTC

HMDB ID

HMDB0015285

Secondary Accession Numbers

HMDB15285

Metabolite Identification

Common Name

Thiamylal

Description

Thiamylal is only found in individuals that have used or taken this drug. It is a barbiturate that is administered intravenously for the production of complete anesthesia of short duration, for the induction of general anesthesia, or for inducing a hypnotic state. (From Martindale, The Extra Pharmacopoeia, 30th ed, p919)Thiamylal 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.

Structure

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

HMDB0015285
     RDKit          3D
Thiamylal
 35 35  0  0  0  0  0  0  0  0999 V2000
   -2.9306    2.4415    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481    1.9923   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7902    0.6196   -0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.2009   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640    0.3850   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978    0.4316   -1.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7903   -0.3149    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    0.3892    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2738   -0.2836    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0334   -0.3148    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.1102    2.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -1.0034    1.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7760   -1.9991    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -2.7981    1.0648 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0046   -2.2674   -0.3903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -1.5673   -0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383   -2.0989   -1.3274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178    3.4640    0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941    1.7912    0.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0121    2.6558   -0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857    0.1131   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7426    0.6637   -1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    1.4507    0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -0.2421   -2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -0.0199   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    1.4437   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533   -1.3966    0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192   -0.2303    1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.4626   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0558    1.4391    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1272    0.4244    0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6172   -1.1260    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -0.6535    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8090   -0.7707    2.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -2.9904   -1.1000 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 15 35  1  0
M  END

1154
  Mrv0541 02231215172D          

 17 17  0  0  1  0            999 V2000
    3.3001   -2.6665    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291   -0.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -0.1915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.4290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -1.4290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -0.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8876    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5376    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5856   -0.6040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.5231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001   -1.8415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    2.6665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2 11  2  0  0  0  0
  3 12  2  0  0  0  0
  4 11  1  0  0  0  0
  4 15  1  0  0  0  0
  5 12  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 11  1  0  0  0  0
  6 12  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8 13  1  0  0  0  0
  9 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015285

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H18N2O2S/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)

> <INCHI_KEY>
XLOMZPUITCYLMJ-UHFFFAOYSA-N

> <FORMULA>
C12H18N2O2S

> <MOLECULAR_WEIGHT>
254.349

> <EXACT_MASS>
254.10889852

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.75344758461245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione

> <ALOGPS_LOGP>
3.11

> <JCHEM_LOGP>
2.923701509666666

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.718430758085919

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.197177099994084

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9999935717190516

> <JCHEM_POLAR_SURFACE_AREA>
58.2

> <JCHEM_REFRACTIVITY>
70.6389

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiamylal

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015285
     RDKit          3D
Thiamylal
 35 35  0  0  0  0  0  0  0  0999 V2000
   -2.9306    2.4415    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481    1.9923   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7902    0.6196   -0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.2009   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640    0.3850   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978    0.4316   -1.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7903   -0.3149    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    0.3892    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2738   -0.2836    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0334   -0.3148    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.1102    2.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -1.0034    1.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7760   -1.9991    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -2.7981    1.0648 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0046   -2.2674   -0.3903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -1.5673   -0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383   -2.0989   -1.3274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178    3.4640    0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941    1.7912    0.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0121    2.6558   -0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857    0.1131   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7426    0.6637   -1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    1.4507    0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -0.2421   -2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -0.0199   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    1.4437   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533   -1.3966    0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192   -0.2303    1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.4626   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0558    1.4391    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1272    0.4244    0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6172   -1.1260    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -0.6535    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8090   -0.7707    2.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -2.9904   -1.1000 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 15 35  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1154                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0       6.160  -4.977   0.000  0.00  0.00           S+0
HETATM    2  O   UNK     0       8.828  -0.357   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.493  -0.357   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       7.494  -2.667   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       4.826  -2.667   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.160  -0.357   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.930   0.976   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.160   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.390   0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.470   0.976   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.494  -1.127   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.826  -1.127   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.930   3.644   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.850   0.976   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.160  -3.437   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.160   4.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   2.310   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   11   15                                                       
CONECT    5   12   15                                                       
CONECT    6    7    9   11   12                                             
CONECT    7    6    8   10                                                  
CONECT    8    7   13                                                       
CONECT    9    6   14                                                       
CONECT   10    7                                                            
CONECT   11    2    4    6                                                  
CONECT   12    3    5    6                                                  
CONECT   13    8   16                                                       
CONECT   14    9   17                                                       
CONECT   15    1    4    5                                                  
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0015285
HETATM    1  C1  UNL     1      -2.931   2.441   0.399  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.848   1.992  -0.201  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.790   0.620  -0.692  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.681  -0.201  -0.064  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.664   0.385  -0.321  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.898   0.432  -1.818  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.790  -0.315   0.350  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.088   0.389   0.011  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.274  -0.284   0.671  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.033  -0.315   1.368  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.397   0.110   2.336  1.00  0.00           O  
HETATM   12  N1  UNL     1      -2.266  -1.003   1.658  1.00  0.00           N  
HETATM   13  C11 UNL     1      -2.776  -1.999   0.777  1.00  0.00           C  
HETATM   14  S1  UNL     1      -4.159  -2.798   1.065  1.00  0.00           S  
HETATM   15  N2  UNL     1      -2.005  -2.267  -0.390  1.00  0.00           N  
HETATM   16  C12 UNL     1      -0.793  -1.567  -0.641  1.00  0.00           C  
HETATM   17  O2  UNL     1       0.138  -2.099  -1.327  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.018   3.464   0.783  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.794   1.791   0.535  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.012   2.656  -0.321  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.786   0.113  -0.497  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.743   0.664  -1.799  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.684   1.451   0.021  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.753  -0.242  -2.124  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.033  -0.020  -2.378  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.116   1.444  -2.191  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.853  -1.397   0.112  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.719  -0.230   1.465  1.00  0.00           H  
HETATM   29  H12 UNL     1       3.300   0.463  -1.064  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.056   1.439   0.392  1.00  0.00           H  
HETATM   31  H14 UNL     1       5.127   0.424   0.730  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.617  -1.126   0.029  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.034  -0.654   1.686  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.809  -0.771   2.544  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.306  -2.990  -1.100  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   20
CONECT    3    4   21   22
CONECT    4    5   10   16
CONECT    5    6    7   23
CONECT    6   24   25   26
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   31   32   33
CONECT   10   11   11   12
CONECT   12   13   34
CONECT   13   14   14   15
CONECT   15   16   35
CONECT   16   17   17
END

HMDB0015285
     RDKit          3D
Thiamylal
 35 35  0  0  0  0  0  0  0  0999 V2000
   -2.9306    2.4415    0.3988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8481    1.9923   -0.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7902    0.6196   -0.6923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6812   -0.2009   -0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6640    0.3850   -0.3215 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978    0.4316   -1.8178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7903   -0.3149    0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0884    0.3892    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2738   -0.2836    0.6713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0334   -0.3148    1.3682 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.1102    2.3357 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2655   -1.0034    1.6583 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7760   -1.9991    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1592   -2.7981    1.0648 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0046   -2.2674   -0.3903 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7933   -1.5673   -0.6411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1383   -2.0989   -1.3274 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0178    3.4640    0.7827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7941    1.7912    0.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0121    2.6558   -0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7857    0.1131   -0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7426    0.6637   -1.7987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6841    1.4507    0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7532   -0.2421   -2.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0332   -0.0199   -2.3783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164    1.4437   -2.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533   -1.3966    0.1120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7192   -0.2303    1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3001    0.4626   -1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0558    1.4391    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1272    0.4244    0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6172   -1.1260    0.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0341   -0.6535    1.6863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8090   -0.7707    2.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064   -2.9904   -1.1000 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
  5  7  1  0
  7  8  1  0
  8  9  1  0
  4 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  4  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 12 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Allyl-5-(1-methylbutyl)-2-thiobarbituric acid	ChEBI
5-Allyl-5-(1-methylbutyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione	ChEBI
5-Allyl-5-(1-methylbutyl)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione	ChEBI
Dihydro-5-(1-methylbutyl)-5-(2-propenyl)-2-thioxo-4,6(1H,5H)-pyrimidinedione	ChEBI
Thioseconal	ChEBI
5-Allyl-5-(1-methylbutyl)-2-thiobarbitate	Generator
5-Allyl-5-(1-methylbutyl)-2-thiobarbitic acid	Generator
Parke davis brand OF thiamylal sodium	HMDB
Thioquinalbarbitone	HMDB
Sodium, thiamylal	HMDB
Surital	HMDB
Thiamylal sodium	HMDB

Chemical Formula

C₁₂H₁₈N₂O₂S

Average Molecular Weight

254.349

Monoisotopic Molecular Weight

254.10889852

IUPAC Name

5-(pentan-2-yl)-5-(prop-2-en-1-yl)-2-sulfanylidene-1,3-diazinane-4,6-dione

Traditional Name

thiamylal

CAS Registry Number

77-27-0

SMILES

CCCC(C)C1(CC=C)C(=O)NC(=S)NC1=O

InChI Identifier

InChI=1S/C12H18N2O2S/c1-4-6-8(3)12(7-5-2)9(15)13-11(17)14-10(12)16/h5,8H,2,4,6-7H2,1,3H3,(H2,13,14,15,16,17)

InChI Key

XLOMZPUITCYLMJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiobarbituric acid derivatives. These are organic compounds containing a 2-thioxodihydropyrimidine-4,6(1H,5H)-dione skeleton.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Thiobarbituric acid derivatives

Alternative Parents

Substituents

Thiobarbiturate
1,3-diazinane
Thiourea
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

barbiturates (CHEBI:9536 )
organosulfur compound (CHEBI:9536 )

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: HMDB0015285)

Source

Exogenous

Exogenous (HMDB: HMDB0015285)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	132 - 133 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.051 g/L	Not Available
LogP	2.5	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.051 g/L	ALOGPS
logP	3.11	ALOGPS
logP	2.92	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	7.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.2 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	70.64 m³·mol⁻¹	ChemAxon
Polarizability	26.75 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]+	158.584	31661259
DarkChem	[M-H]-	153.411	31661259
DeepCCS	[M+H]+	159.27	30932474
DeepCCS	[M-H]-	156.912	30932474
DeepCCS	[M-2H]-	190.774	30932474
DeepCCS	[M+Na]+	166.415	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	154.4	32859911
AllCCS	[M+NH4]+	161.4	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	161.2	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Thiamylal	CCCC(C)C1(CC=C)C(=O)NC(=S)NC1=O	3650.9	Standard polar	33892256
Thiamylal	CCCC(C)C1(CC=C)C(=O)NC(=S)NC1=O	1852.9	Standard non polar	33892256
Thiamylal	CCCC(C)C1(CC=C)C(=O)NC(=S)NC1=O	2020.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Thiamylal,1TMS,isomer #1	C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C)C1=O	1925.5	Semi standard non polar	33892256
Thiamylal,1TMS,isomer #1	C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C)C1=O	2062.7	Standard non polar	33892256
Thiamylal,1TMS,isomer #1	C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C)C1=O	3131.0	Standard polar	33892256
Thiamylal,2TMS,isomer #1	C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C)C(=S)N([Si](C)(C)C)C1=O	1908.0	Semi standard non polar	33892256
Thiamylal,2TMS,isomer #1	C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C)C(=S)N([Si](C)(C)C)C1=O	2089.6	Standard non polar	33892256
Thiamylal,2TMS,isomer #1	C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C)C(=S)N([Si](C)(C)C)C1=O	2618.0	Standard polar	33892256
Thiamylal,1TBDMS,isomer #1	C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C(C)(C)C)C1=O	2109.4	Semi standard non polar	33892256
Thiamylal,1TBDMS,isomer #1	C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C(C)(C)C)C1=O	2286.6	Standard non polar	33892256
Thiamylal,1TBDMS,isomer #1	C=CCC1(C(C)CCC)C(=O)NC(=S)N([Si](C)(C)C(C)(C)C)C1=O	3151.4	Standard polar	33892256
Thiamylal,2TBDMS,isomer #1	C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C(C)(C)C)C(=S)N([Si](C)(C)C(C)(C)C)C1=O	2338.5	Semi standard non polar	33892256
Thiamylal,2TBDMS,isomer #1	C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C(C)(C)C)C(=S)N([Si](C)(C)C(C)(C)C)C1=O	2510.1	Standard non polar	33892256
Thiamylal,2TBDMS,isomer #1	C=CCC1(C(C)CCC)C(=O)N([Si](C)(C)C(C)(C)C)C(=S)N([Si](C)(C)C(C)(C)C)C1=O	2723.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Thiamylal CI-B (Non-derivatized)	splash10-0a4i-0090000000-8766fbc86b0e4f9df12c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Thiamylal CI-B (Non-derivatized)	splash10-0a4i-0090000000-8766fbc86b0e4f9df12c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamylal GC-MS (Non-derivatized) - 70eV, Positive	splash10-01y6-9270000000-c654329959eddd973209	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Thiamylal 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 - Thiamylal 10V, Positive-QTOF	splash10-0a4i-1190000000-0e3bd0fbb412c080adfc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 20V, Positive-QTOF	splash10-0909-1790000000-b4f2b35dea5c7d7b95f2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 40V, Positive-QTOF	splash10-008c-9200000000-b0f2760a6b889d0deb0d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 10V, Negative-QTOF	splash10-0w29-2490000000-c2215a8fd83ef9a5da9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 20V, Negative-QTOF	splash10-0a4i-9010000000-a4d75b8b0d44951d26fb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 40V, Negative-QTOF	splash10-0a4i-9200000000-7598e665b19cdbc1f0d3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 10V, Positive-QTOF	splash10-052r-0960000000-7fcdb946d222ec5772f4	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 20V, Positive-QTOF	splash10-0a4r-1970000000-920b6209dda20032e20c	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 40V, Positive-QTOF	splash10-01c9-3900000000-1d0ac0f9a99fbc906469	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 10V, Negative-QTOF	splash10-0udi-0090000000-5f9d4ba9eb406a9469e2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 20V, Negative-QTOF	splash10-052f-9120000000-7d2c2f1d657b97b34a50	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Thiamylal 40V, Negative-QTOF	splash10-0a4i-9500000000-32f064b826d15da527c1	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 DB01154	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01154	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01154

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2297298

KEGG Compound ID

C07846

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Thiamylal

METLIN ID

Not Available

PubChem Compound

3032285

PDB ID

Not Available

ChEBI ID

9536

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. ATP-sensitive inward rectifier potassium channel 11

General function:: Involved in inward rectifier potassium channel activity
Specific function:: This receptor is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by extracellular barium
Gene Name:: KCNJ11
Uniprot ID:: Q14654
Molecular weight:: 43540.4

References

Kawano T, Oshita S, Takahashi A, Tsutsumi Y, Tomiyama Y, Kitahata H, Kuroda Y, Nakaya Y: Molecular mechanisms of the inhibitory effects of propofol and thiamylal on sarcolemmal adenosine triphosphate-sensitive potassium channels. Anesthesiology. 2004 Feb;100(2):338-46. [PubMed:14739809 ]
Tsutsumi Y, Oshita S, Kitahata H, Kuroda Y, Kawano T, Nakaya Y: Blockade of adenosine triphosphate-sensitive potassium channels by thiamylal in rat ventricular myocytes. Anesthesiology. 2000 Apr;92(4):1154-9. [PubMed:10754636 ]
Eguchi S, Kawano T, Oshita S, Nakajo N: [Effects of propofol and thiamylal on nicorandil induced ATP-sensitive potassium channel activities in cultured rat aortic smooth muscle cells]. Masui. 2005 Apr;54(4):364-9. [PubMed:15852621 ]

Enzyme Details

2. 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

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 ]
Sugimura M, Kitayama S, Morita K, Imai Y, Irifune M, Takarada T, Kawahara M, Dohi T: Effects of GABAergic agents on anesthesia induced by halothane, isoflurane, and thiamylal in mice. Pharmacol Biochem Behav. 2002 May;72(1-2):111-6. [PubMed:11900777 ]
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 ]
Grasshoff C, Netzhammer N, Schweizer J, Antkowiak B, Hentschke H: Depression of spinal network activity by thiopental: shift from phasic to tonic GABA(A) receptor-mediated inhibition. Neuropharmacology. 2008 Oct;55(5):793-802. doi: 10.1016/j.neuropharm.2008.06.026. Epub 2008 Jun 21. [PubMed:18619475 ]

Enzyme Details

3. ATP-sensitive inward rectifier potassium channel 8

General function:: Involved in inward rectifier potassium channel activity
Specific function:: This potassium channel is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by external barium
Gene Name:: KCNJ8
Uniprot ID:: Q15842
Molecular weight:: 47967.5

References

Eguchi S, Kawano T, Oshita S, Nakajo N: [Effects of propofol and thiamylal on nicorandil induced ATP-sensitive potassium channel activities in cultured rat aortic smooth muscle cells]. Masui. 2005 Apr;54(4):364-9. [PubMed:15852621 ]
Kawano T, Oshita S, Takahashi A, Tsutsumi Y, Tomiyama Y, Kitahata H, Kuroda Y, Nakaya Y: Molecular mechanisms of the inhibitory effects of propofol and thiamylal on sarcolemmal adenosine triphosphate-sensitive potassium channels. Anesthesiology. 2004 Feb;100(2):338-46. [PubMed:14739809 ]
Tsutsumi Y, Oshita S, Kitahata H, Kuroda Y, Kawano T, Nakaya Y: Blockade of adenosine triphosphate-sensitive potassium channels by thiamylal in rat ventricular myocytes. Anesthesiology. 2000 Apr;92(4):1154-9. [PubMed:10754636 ]

Showing metabocard for Thiamylal (HMDB0015285)

MOL for HMDB0015285 (Thiamylal)

3D MOL for HMDB0015285 (Thiamylal)

3D SDF for HMDB0015285 (Thiamylal)

3D-SDF for HMDB0015285 (Thiamylal)

PDB for HMDB0015285 (Thiamylal)

3D PDB for HMDB0015285 (Thiamylal)

SMILES for HMDB0015285 (Thiamylal)

INCHI for HMDB0015285 (Thiamylal)

Structure for HMDB0015285 (Thiamylal)

3D Structure for HMDB0015285 (Thiamylal)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References