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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

2023-02-21 17:18:29 UTC

HMDB ID

HMDB0015441

Secondary Accession Numbers

HMDB15441

Metabolite Identification

Common Name

Aprobarbital

Description

Aprobarbital, also known as allypropymal or alurate, 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. Aprobarbital is a very weakly acidic compound (based on its pKa). Aprobarbital was never as widely used as more common barbiturate derivatives such as phenobarbital and is now rarely prescribed as it has been replaced by newer drugs with a better safety margin. It has sedative, hypnotic and anticonvulsant properties, and was used primarily for the treatment of insomnia. Aprobarbital (or aprobarbitone), sold as Oramon, Somnifaine, and Allonal, is a barbiturate derivative invented in the 1920s by Ernst Preiswerk.

Structure

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

HMDB0015441
     RDKit          3D
Aprobarbital
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.3178    1.0936   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572    0.5912    0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557   -0.4973   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -0.1089   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294   -1.2692   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2142   -0.9822   -0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4543   -2.5393    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    0.2310    1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.5011    2.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.3407    1.6556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3839    2.2897    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    3.2910    0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9296    2.1528   -0.6456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241    1.0522   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.0578   -2.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    0.7329   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    1.8823   -0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4275    0.9782    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893   -0.8022   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484   -1.3659    0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -1.4545   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820   -0.3815    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.4646   -1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -1.9230   -0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371   -2.4672    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -3.2733   -0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -3.0201   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025    1.4831    2.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019    2.8738   -1.3411 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
  4  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  4  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 13 29  1  0
M  END


  Mrv0541 02231215242D          

 15 15  0  0  0  0            999 V2000
    1.8569   -2.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2695   -1.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8569   -1.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -1.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6820   -2.6352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -3.3497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0945   -1.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3800   -0.6832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8089   -0.6832    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5234   -1.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2379   -0.6832    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5234   -1.9208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8089   -2.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8089   -3.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6820   -4.0642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 13  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15  6  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015441

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)

> <INCHI_KEY>
UORJNBVJVRLXMQ-UHFFFAOYSA-N

> <FORMULA>
C10H14N2O3

> <MOLECULAR_WEIGHT>
210.2298

> <EXACT_MASS>
210.100442324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.498060321197006

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.144694595333333

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.148448193028818

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.478869260649752

> <JCHEM_POLAR_SURFACE_AREA>
75.27000000000001

> <JCHEM_REFRACTIVITY>
53.446

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
aprobarbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015441
     RDKit          3D
Aprobarbital
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.3178    1.0936   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572    0.5912    0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557   -0.4973   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -0.1089   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294   -1.2692   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2142   -0.9822   -0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4543   -2.5393    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    0.2310    1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.5011    2.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.3407    1.6556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3839    2.2897    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    3.2910    0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9296    2.1528   -0.6456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241    1.0522   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.0578   -2.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    0.7329   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    1.8823   -0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4275    0.9782    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893   -0.8022   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484   -1.3659    0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -1.4545   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820   -0.3815    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.4646   -1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -1.9230   -0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371   -2.4672    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -3.2733   -0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -3.0201   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025    1.4831    2.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019    2.8738   -1.3411 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
  4  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  4  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 13 29  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0       3.466  -4.919   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.236  -3.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.466  -2.252   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.776  -3.585   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.006  -4.919   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.776  -6.253   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.776  -2.045   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.443  -1.275   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0       7.110  -1.275   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       8.444  -2.045   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.777  -1.275   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       8.444  -3.585   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       7.110  -4.355   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.110  -5.895   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.006  -7.587   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    7   13                                             
CONECT    5    4    6                                                       
CONECT    6    5   15                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13    4   12   14                                                  
CONECT   14   13                                                            
CONECT   15    6                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0015441
HETATM    1  C1  UNL     1       3.318   1.094  -0.608  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.457   0.591   0.245  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.556  -0.497  -0.218  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.098  -0.109  -0.099  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.729  -1.269  -0.590  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.214  -0.982  -0.513  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.454  -2.539   0.152  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.228   0.231   1.299  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.237  -0.501   2.238  1.00  0.00           O  
HETATM   10  N1  UNL     1      -1.040   1.341   1.656  1.00  0.00           N  
HETATM   11  C9  UNL     1      -1.384   2.290   0.686  1.00  0.00           C  
HETATM   12  O2  UNL     1      -2.108   3.291   0.977  1.00  0.00           O  
HETATM   13  N2  UNL     1      -0.930   2.153  -0.646  1.00  0.00           N  
HETATM   14  C10 UNL     1      -0.124   1.052  -1.000  1.00  0.00           C  
HETATM   15  O3  UNL     1       0.428   1.058  -2.128  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.376   0.733  -1.620  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.983   1.882  -0.302  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.428   0.978   1.252  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.789  -0.802  -1.255  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.748  -1.366   0.456  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.474  -1.455  -1.663  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.482  -0.381   0.379  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.562  -0.465  -1.450  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.800  -1.923  -0.452  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.537  -2.467   1.240  1.00  0.00           H  
HETATM   26  H11 UNL     1      -1.251  -3.273  -0.167  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.504  -3.020  -0.184  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.402   1.483   2.639  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.202   2.874  -1.341  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   18
CONECT    3    4   19   20
CONECT    4    5    8   14
CONECT    5    6    7   21
CONECT    6   22   23   24
CONECT    7   25   26   27
CONECT    8    9    9   10
CONECT   10   11   28
CONECT   11   12   12   13
CONECT   13   14   29
CONECT   14   15   15
END

HMDB0015441
     RDKit          3D
Aprobarbital
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.3178    1.0936   -0.6080 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4572    0.5912    0.2453 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557   -0.4973   -0.2182 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0983   -0.1089   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7294   -1.2692   -0.5901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2142   -0.9822   -0.5130 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4543   -2.5393    0.1516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2281    0.2310    1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2369   -0.5011    2.2384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0403    1.3407    1.6556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3839    2.2897    0.6856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1083    3.2910    0.9775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9296    2.1528   -0.6456 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1241    1.0522   -1.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4275    1.0578   -2.1279 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3763    0.7329   -1.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9834    1.8823   -0.3019 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4275    0.9782    1.2518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7893   -0.8022   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7484   -1.3659    0.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -1.4545   -1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820   -0.3815    0.3786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5616   -0.4646   -1.4497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7997   -1.9230   -0.4523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5371   -2.4672    1.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2513   -3.2733   -0.1672 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -3.0201   -0.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4025    1.4831    2.6387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2019    2.8738   -1.3411 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
  4  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  4  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  3 20  1  0
  5 21  1  0
  6 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 13 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
5-(1-Methylethyl)-5-(2-propenyl)-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Allyl-5-isopropylbarbituric acid	ChEBI
5-Allyl-5-isopropylpyrimidine-2,4,6(1H,3H,5H)-trione	ChEBI
5-Isopropyl-5-allylbarbituric acid	ChEBI
Allypropymal	ChEBI
Alurate	ChEBI
5-Allyl-5-isopropylbarbitate	Generator
5-Allyl-5-isopropylbarbitic acid	Generator
5-Isopropyl-5-allylbarbitate	Generator
5-Isopropyl-5-allylbarbitic acid	Generator
Aluric acid	Generator
Alate	HMDB
Alic acid	HMDB
Allylpropymal	HMDB
Aprobarbitone	HMDB
Allylpropymal, monosodium salt	HMDB

Chemical Formula

C₁₀H₁₄N₂O₃

Average Molecular Weight

210.2298

Monoisotopic Molecular Weight

210.100442324

IUPAC Name

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

Traditional Name

aprobarbital

CAS Registry Number

77-02-1

SMILES

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

InChI Identifier

InChI=1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15)

InChI Key

UORJNBVJVRLXMQ-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:2791 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0015441)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	141 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5.17 g/L	Not Available
LogP	1.15	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	5.17 g/L	ALOGPS
logP	1.24	ALOGPS
logP	1.14	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	8.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.27 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	53.45 m³·mol⁻¹	ChemAxon
Polarizability	20.5 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]+	148.116	31661259
DarkChem	[M-H]-	144.141	31661259
DeepCCS	[M+H]+	147.807	30932474
DeepCCS	[M-H]-	143.979	30932474
DeepCCS	[M-2H]-	181.427	30932474
DeepCCS	[M+Na]+	156.966	30932474
AllCCS	[M+H]+	146.4	32859911
AllCCS	[M+H-H2O]+	142.5	32859911
AllCCS	[M+NH4]+	150.1	32859911
AllCCS	[M+Na]+	151.1	32859911
AllCCS	[M-H]-	147.3	32859911
AllCCS	[M+Na-2H]-	148.0	32859911
AllCCS	[M+HCOO]-	148.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aprobarbital	CC(C)C1(CC=C)C(=O)NC(=O)NC1=O	2916.0	Standard polar	33892256
Aprobarbital	CC(C)C1(CC=C)C(=O)NC(=O)NC1=O	1605.5	Standard non polar	33892256
Aprobarbital	CC(C)C1(CC=C)C(=O)NC(=O)NC1=O	1606.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aprobarbital,1TMS,isomer #1	C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1609.1	Semi standard non polar	33892256
Aprobarbital,1TMS,isomer #1	C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O	1763.8	Standard non polar	33892256
Aprobarbital,1TMS,isomer #1	C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2663.9	Standard polar	33892256
Aprobarbital,2TMS,isomer #1	C=CCC1(C(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1570.6	Semi standard non polar	33892256
Aprobarbital,2TMS,isomer #1	C=CCC1(C(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	1820.4	Standard non polar	33892256
Aprobarbital,2TMS,isomer #1	C=CCC1(C(C)C)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2212.2	Standard polar	33892256
Aprobarbital,1TBDMS,isomer #1	C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1816.5	Semi standard non polar	33892256
Aprobarbital,1TBDMS,isomer #1	C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	1991.8	Standard non polar	33892256
Aprobarbital,1TBDMS,isomer #1	C=CCC1(C(C)C)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2706.9	Standard polar	33892256
Aprobarbital,2TBDMS,isomer #1	C=CCC1(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2018.0	Semi standard non polar	33892256
Aprobarbital,2TBDMS,isomer #1	C=CCC1(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2251.5	Standard non polar	33892256
Aprobarbital,2TBDMS,isomer #1	C=CCC1(C(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2361.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Aprobarbital EI-B (Non-derivatized)	splash10-014l-9600000000-9ab2ab6ff36ccb20312f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Aprobarbital CI-B (Non-derivatized)	splash10-03di-0090000000-b13a014a6928d0747567	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Aprobarbital EI-B (Non-derivatized)	splash10-014l-9600000000-9ab2ab6ff36ccb20312f	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Aprobarbital CI-B (Non-derivatized)	splash10-03di-0090000000-b13a014a6928d0747567	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aprobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-00kf-6900000000-8e2fadd8c703abf57cab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aprobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Aprobarbital 35V, Negative-QTOF	splash10-052g-9340000000-7606e92a526391d4fe69	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 10V, Positive-QTOF	splash10-03di-0390000000-181ed7f48a6f8b2be459	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 20V, Positive-QTOF	splash10-0005-4900000000-c3ed55bedff14b2893f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 40V, Positive-QTOF	splash10-000x-9000000000-7921b62ac5b52f86c373	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 10V, Negative-QTOF	splash10-05mo-8950000000-b232a6440f5538b1f92e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 20V, Negative-QTOF	splash10-0006-9500000000-7ed9cf57a53d84095449	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 40V, Negative-QTOF	splash10-0007-9200000000-55c099997913083a521f	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 10V, Positive-QTOF	splash10-03di-0790000000-0080941b73c060d0c3ea	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 20V, Positive-QTOF	splash10-052b-9210000000-bb699f2867a4017b84e1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 40V, Positive-QTOF	splash10-0a4j-9100000000-37fda3df56bd06c65a0a	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 10V, Negative-QTOF	splash10-0a4i-2390000000-5fc08243ebac6ecef3e1	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 20V, Negative-QTOF	splash10-0006-9100000000-6264c5b2cdaf4d9ea453	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aprobarbital 40V, Negative-QTOF	splash10-0006-9400000000-6f85e6486e25545f181a	2021-10-11	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX 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 DB01352	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01352	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01352

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

6221

KEGG Compound ID

C07826

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Aprobarbital

METLIN ID

Not Available

PubChem Compound

6464

PDB ID

Not Available

ChEBI ID

2791

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 Aprobarbital (HMDB0015441)

MOL for HMDB0015441 (Aprobarbital)

3D MOL for HMDB0015441 (Aprobarbital)

3D SDF for HMDB0015441 (Aprobarbital)

3D-SDF for HMDB0015441 (Aprobarbital)

PDB for HMDB0015441 (Aprobarbital)

3D PDB for HMDB0015441 (Aprobarbital)

SMILES for HMDB0015441 (Aprobarbital)

INCHI for HMDB0015441 (Aprobarbital)

Structure for HMDB0015441 (Aprobarbital)

3D Structure for HMDB0015441 (Aprobarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

References

References

References

References

References

References

References

References