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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

HMDB0015443

Secondary Accession Numbers

HMDB15443

Metabolite Identification

Common Name

Heptabarbital

Description

Heptabarbital is only found in individuals that have used or taken this drug. It is an intermediate or short term barbiturate used mainly for sedation and hypnosis.Heptabarbital (like all barbiturates) works by binding to the GABAA receptor at either the alpha or the beta sub unit. These are binding sites that are distinct from GABA itself and also distinct from the benzodiazepine binding site. Like benzodiazepines, barbiturates potentiate the effect of GABA at this receptor. This GABAA receptor binding decreases input resistance, depresses burst and tonic firing, especially in ventrobasal and intralaminar neurons, while at the same time increasing burst duration and mean conductance at individual chloride channels; this increases both the amplitude and decay time of inhibitory postsynaptic currents. In addition to this GABA-ergic effect, barbiturates also block the AMPA receptor, a subtype of glutamate receptor. Glutamate is the principal excitatory neurotransmitter in the mammalian CNS. Heptabarbital also appears to bind neuronal nicotinic acetylcholine receptors.

Structure

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

HMDB0015443
     RDKit          3D
Heptabarbital
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.6080    0.2098    2.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8548   -0.5063    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953   -0.0422   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -0.1567   -0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -1.2882   -0.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3746   -1.6193   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249   -0.4223   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872    0.2942    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    0.4433    1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    0.9555    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181   -0.6892   -1.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073   -1.3533   -2.4705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0449   -0.5589   -1.9093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836    0.6510   -1.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.8485   -1.7365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833    1.6313   -0.8723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    1.4234   -0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7363    2.3716   -0.6023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.1081    2.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.1623    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877    1.3000    2.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -0.4714    0.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -1.5984    1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095   -2.0947   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.9956    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -2.4432   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604    0.3041   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -0.7659   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1415   -0.3773    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0080    1.2441    0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9112   -0.5236    1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3933    1.1773    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666    1.4660    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5263    1.6420   -0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -1.3282   -2.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3469    2.5429   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17  3  1  0
 10  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 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
 10 33  1  0
 10 34  1  0
 13 35  1  0
 16 36  1  0
M  END

1354
  Mrv0541 02231215242D          

 18 19  0  0  0  0            999 V2000
    3.5679   -1.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9969    1.3976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4258   -1.0775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9969   -1.0775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7113    0.1601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823    0.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4573    0.1601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994    0.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950    1.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8698    0.8745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0994   -0.5833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2950   -0.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823   -0.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9969    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2823    1.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7113   -0.6650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 15  2  0  0  0  0
  2 16  2  0  0  0  0
  3 18  2  0  0  0  0
  4 15  1  0  0  0  0
  4 18  1  0  0  0  0
  5 16  1  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  6 15  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  2  0  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 17  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015443

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O3/c1-2-13(9-7-5-3-4-6-8-9)10(16)14-12(18)15-11(13)17/h7H,2-6,8H2,1H3,(H2,14,15,16,17,18)

> <INCHI_KEY>
PAZQYDJGLKSCSI-UHFFFAOYSA-N

> <FORMULA>
C13H18N2O3

> <MOLECULAR_WEIGHT>
250.2936

> <EXACT_MASS>
250.131742452

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
25.857658484912278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
1.9130831926666663

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.806314442929297

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.140078077502258

> <JCHEM_POLAR_SURFACE_AREA>
75.27

> <JCHEM_REFRACTIVITY>
66.2527

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
heptabarbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015443
     RDKit          3D
Heptabarbital
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.6080    0.2098    2.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8548   -0.5063    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953   -0.0422   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -0.1567   -0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -1.2882   -0.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3746   -1.6193   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249   -0.4223   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872    0.2942    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    0.4433    1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    0.9555    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181   -0.6892   -1.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073   -1.3533   -2.4705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0449   -0.5589   -1.9093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836    0.6510   -1.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.8485   -1.7365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833    1.6313   -0.8723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    1.4234   -0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7363    2.3716   -0.6023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.1081    2.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.1623    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877    1.3000    2.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -0.4714    0.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -1.5984    1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095   -2.0947   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.9956    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -2.4432   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604    0.3041   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -0.7659   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1415   -0.3773    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0080    1.2441    0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9112   -0.5236    1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3933    1.1773    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666    1.4660    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5263    1.6420   -0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -1.3282   -2.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3469    2.5429   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17  3  1  0
 10  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 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
 10 33  1  0
 10 34  1  0
 13 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1354                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       6.660  -2.011   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       9.328   2.609   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      11.995  -2.011   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.328  -2.011   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      10.661   0.299   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       7.994   0.299   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.454   0.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.786   1.686   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.284   2.029   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.224   1.632   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080   1.069   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.080  -0.471   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.786  -1.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.284  -1.432   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.994  -1.241   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.328   1.069   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.994   2.966   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.661  -1.241   0.000  0.00  0.00           C+0
CONECT    1   15                                                            
CONECT    2   16                                                            
CONECT    3   18                                                            
CONECT    4   15   18                                                       
CONECT    5   16   18                                                       
CONECT    6    7   10   15   16                                             
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   11                                                       
CONECT   10    6   17                                                       
CONECT   11    9   12                                                       
CONECT   12   11   14                                                       
CONECT   13    7   14                                                       
CONECT   14   12   13                                                       
CONECT   15    1    4    6                                                  
CONECT   16    2    5    6                                                  
CONECT   17   10                                                            
CONECT   18    3    4    5                                                  
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0015443
HETATM    1  C1  UNL     1      -1.608   0.210   2.088  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.855  -0.506   0.819  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.095  -0.042  -0.391  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.327  -0.157  -0.199  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.903  -1.288  -0.600  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.375  -1.619  -0.500  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.225  -0.422  -0.748  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.487   0.294   0.572  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.199   0.443   1.360  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.072   0.955   0.516  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.618  -0.689  -1.614  1.00  0.00           C  
HETATM   12  O1  UNL     1      -1.007  -1.353  -2.471  1.00  0.00           O  
HETATM   13  N1  UNL     1      -3.045  -0.559  -1.909  1.00  0.00           N  
HETATM   14  C12 UNL     1      -3.684   0.651  -1.518  1.00  0.00           C  
HETATM   15  O2  UNL     1      -4.924   0.848  -1.737  1.00  0.00           O  
HETATM   16  N2  UNL     1      -2.883   1.631  -0.872  1.00  0.00           N  
HETATM   17  C13 UNL     1      -1.501   1.423  -0.621  1.00  0.00           C  
HETATM   18  O3  UNL     1      -0.736   2.372  -0.602  1.00  0.00           O  
HETATM   19  H1  UNL     1      -0.669  -0.108   2.573  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.409  -0.162   2.814  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.788   1.300   2.077  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.961  -0.471   0.616  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.650  -1.598   1.026  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.310  -2.095  -1.014  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.517  -1.996   0.530  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.598  -2.443  -1.188  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.760   0.304  -1.440  1.00  0.00           H  
HETATM   28  H10 UNL     1       4.219  -0.766  -1.124  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.142  -0.377   1.165  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.008   1.244   0.441  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.911  -0.524   1.805  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.393   1.177   2.162  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.367   1.466   1.181  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.526   1.642  -0.237  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.560  -1.328  -2.387  1.00  0.00           H  
HETATM   36  H18 UNL     1      -3.347   2.543  -0.574  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   11   17
CONECT    4    5    5   10
CONECT    5    6   24
CONECT    6    7   25   26
CONECT    7    8   27   28
CONECT    8    9   29   30
CONECT    9   10   31   32
CONECT   10   33   34
CONECT   11   12   12   13
CONECT   13   14   35
CONECT   14   15   15   16
CONECT   16   17   36
CONECT   17   18   18
END

HMDB0015443
     RDKit          3D
Heptabarbital
 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.6080    0.2098    2.0876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8548   -0.5063    0.8194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0953   -0.0422   -0.3913 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3270   -0.1567   -0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9026   -1.2882   -0.6004 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3746   -1.6193   -0.5002 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249   -0.4223   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872    0.2942    0.5715 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1990    0.4433    1.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    0.9555    0.5163 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181   -0.6892   -1.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0073   -1.3533   -2.4705 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0449   -0.5589   -1.9093 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6836    0.6510   -1.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9237    0.8485   -1.7365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833    1.6313   -0.8723 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5007    1.4234   -0.6215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7363    2.3716   -0.6023 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6691   -0.1081    2.5733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.1623    2.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7877    1.3000    2.0769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -0.4714    0.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499   -1.5984    1.0263 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095   -2.0947   -1.0144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5171   -1.9956    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5981   -2.4432   -1.1876 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7604    0.3041   -1.4397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2191   -0.7659   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1415   -0.3773    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0080    1.2441    0.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9112   -0.5236    1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3933    1.1773    2.1616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3666    1.4660    1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5263    1.6420   -0.2367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5596   -1.3282   -2.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3469    2.5429   -0.5739 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17  3  1  0
 10  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  2 23  1  0
  5 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
 10 33  1  0
 10 34  1  0
 13 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Heptabarb	HMDB
Heptabarbitone	HMDB
Heptabarbum	HMDB
Heptadorm	HMDB
Heptamal	HMDB
Heptamalum	HMDB
Heptbarbital	HMDB
Medapan	HMDB
Medomine	HMDB
Heptabarbital, monosodium salt	HMDB
Medomin	HMDB

Chemical Formula

C₁₃H₁₈N₂O₃

Average Molecular Weight

250.2936

Monoisotopic Molecular Weight

250.131742452

IUPAC Name

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

Traditional Name

heptabarbital

CAS Registry Number

509-86-4

SMILES

CCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC1

InChI Identifier

InChI=1S/C13H18N2O3/c1-2-13(9-7-5-3-4-6-8-9)10(16)14-12(18)15-11(13)17/h7H,2-6,8H2,1H3,(H2,14,15,16,17,18)

InChI Key

PAZQYDJGLKSCSI-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:81297 )

Ontology

Not Available

Urine (PMID: 21059682)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0015443)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	174 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.32 g/L	Not Available
LogP	2.03	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.32 g/L	ALOGPS
logP	2.41	ALOGPS
logP	1.91	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	8.14	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	66.25 m³·mol⁻¹	ChemAxon
Polarizability	25.86 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.876	31661259
DarkChem	[M-H]-	155.814	31661259
DeepCCS	[M+H]+	168.31	30932474
DeepCCS	[M-H]-	165.952	30932474
DeepCCS	[M-2H]-	198.838	30932474
DeepCCS	[M+Na]+	174.403	30932474
AllCCS	[M+H]+	158.2	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	161.7	32859911
AllCCS	[M+Na]+	162.7	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	161.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heptabarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC1	3432.1	Standard polar	33892256
Heptabarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC1	2002.6	Standard non polar	33892256
Heptabarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CCCCCC1	2059.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heptabarbital,1TMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2135.6	Semi standard non polar	33892256
Heptabarbital,1TMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2213.1	Standard non polar	33892256
Heptabarbital,1TMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	3180.9	Standard polar	33892256
Heptabarbital,2TMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2065.5	Semi standard non polar	33892256
Heptabarbital,2TMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2240.6	Standard non polar	33892256
Heptabarbital,2TMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2854.4	Standard polar	33892256
Heptabarbital,1TBDMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2340.1	Semi standard non polar	33892256
Heptabarbital,1TBDMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2441.0	Standard non polar	33892256
Heptabarbital,1TBDMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	3285.0	Standard polar	33892256
Heptabarbital,2TBDMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2479.4	Semi standard non polar	33892256
Heptabarbital,2TBDMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2696.7	Standard non polar	33892256
Heptabarbital,2TBDMS,isomer #1	CCC1(C2=CCCCCC2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2981.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Heptabarbital CI-B (Non-derivatized)	splash10-0udi-0090000000-65df1d705dbf292d1920	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Heptabarbital EI-B (Non-derivatized)	splash10-00di-7490000000-252904343000182d024d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Heptabarbital CI-B (Non-derivatized)	splash10-0udi-0090000000-65df1d705dbf292d1920	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Heptabarbital EI-B (Non-derivatized)	splash10-00di-7490000000-252904343000182d024d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heptabarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fr-4490000000-f676a100f3d6debe336f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heptabarbital 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 - Heptabarbital 10V, Positive-QTOF	splash10-0udi-1190000000-9cf7406553f0c3090d2b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 20V, Positive-QTOF	splash10-001r-0920000000-354a96c2de9379d61ff7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 40V, Positive-QTOF	splash10-0007-9100000000-b3896ac0c48273f3b1dc	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 10V, Negative-QTOF	splash10-052g-6290000000-4db48fb035bc3dc01a83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 20V, Negative-QTOF	splash10-0006-9520000000-b1174b032510d606f67b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 40V, Negative-QTOF	splash10-000x-9500000000-a779572754d9ebabf849	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 10V, Positive-QTOF	splash10-0udi-0090000000-6837e1e1e3c9db8cb828	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 20V, Positive-QTOF	splash10-000j-3920000000-5838db34fbb1cb18a957	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 40V, Positive-QTOF	splash10-0a4s-6910000000-ef411a5f84c216e4a389	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 10V, Negative-QTOF	splash10-002o-6940000000-86c999fda1134290fded	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 20V, Negative-QTOF	splash10-0006-9210000000-9694a6b9a7cdd874a66a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heptabarbital 40V, Negative-QTOF	splash10-0006-9400000000-8a3aea06bcf2795addf5	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 DB01354	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01354	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01354

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10081

KEGG Compound ID

C17725

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Heptabarb

METLIN ID

Not Available

PubChem Compound

10518

PDB ID

Not Available

ChEBI ID

588074

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 ]

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 Heptabarbital (HMDB0015443)

MOL for HMDB0015443 (Heptabarbital)

3D MOL for HMDB0015443 (Heptabarbital)

3D SDF for HMDB0015443 (Heptabarbital)

3D-SDF for HMDB0015443 (Heptabarbital)

PDB for HMDB0015443 (Heptabarbital)

3D PDB for HMDB0015443 (Heptabarbital)

SMILES for HMDB0015443 (Heptabarbital)

INCHI for HMDB0015443 (Heptabarbital)

Structure for HMDB0015443 (Heptabarbital)

3D Structure for HMDB0015443 (Heptabarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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