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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-06-12 17:32:37 UTC

Update Date

2019-07-23 07:14:33 UTC

HMDB ID

HMDB0060537

Secondary Accession Numbers

HMDB60537

Metabolite Identification

Common Name

p-Hydroxyphenobarbital

Description

p-Hydroxyphenobarbital, also known as p-hydroxy-PB, 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. p-Hydroxyphenobarbital is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0060537
     RDKit          3D
p-Hydroxyphenobarbital
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.0240    1.7365    1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1492    0.2294    1.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -0.2951   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    0.0867   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2312    0.9695   -1.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825    1.2598   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    0.6382   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.9570   -0.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599   -0.2603    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -0.5395    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144   -1.7994   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1303   -2.5892   -0.1171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287   -2.3038    0.2197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618   -1.5711   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358   -2.0042   -0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085   -0.3458   -0.9042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6498    0.1233   -1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.8281   -2.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    2.1421    1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4242    2.0349    2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176    2.1558    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -0.1078    1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -0.2290    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.4844   -1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277    1.9740   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3767    0.4014   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559   -0.7467    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.2450    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508   -3.2195    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8202    0.2351   -1.2610 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  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
  8 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 16 30  1  0
M  END

[NO NAME]
  Mrv0541 04171217172D          
Created with ChemWriter - http://chemwriter.com
 18 19  0  0  0  0            999 V2000
    1.6500    0.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.1658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.3092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6665    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8415    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    0.8803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4916    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291    1.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3166    2.3092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7291    3.0237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3 14  2  0  0  0  0
  4  9  1  0  0  0  0
  4 14  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6  9  1  0  0  0  0
  6 10  1  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  8 13  1  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 15 17  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060537

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O4/c1-2-12(7-3-5-8(15)6-4-7)9(16)13-11(18)14-10(12)17/h3-6,15H,2H2,1H3,(H2,13,14,16,17,18)

> <INCHI_KEY>
IEPXMKJNWPXDBP-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O4

> <MOLECULAR_WEIGHT>
248.2347

> <EXACT_MASS>
248.079706882

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
23.60993701193366

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
1.1027648063333333

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.503805034137098

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.117519918499331

> <JCHEM_PKA_STRONGEST_BASIC>
-5.959023595626221

> <JCHEM_POLAR_SURFACE_AREA>
95.5

> <JCHEM_REFRACTIVITY>
61.7272

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethyl-5-(4-hydroxyphenyl)-1,3-diazinane-2,4,6-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0060537
     RDKit          3D
p-Hydroxyphenobarbital
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.0240    1.7365    1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1492    0.2294    1.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -0.2951   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    0.0867   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2312    0.9695   -1.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825    1.2598   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    0.6382   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.9570   -0.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599   -0.2603    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -0.5395    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144   -1.7994   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1303   -2.5892   -0.1171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287   -2.3038    0.2197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618   -1.5711   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358   -2.0042   -0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085   -0.3458   -0.9042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6498    0.1233   -1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.8281   -2.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    2.1421    1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4242    2.0349    2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176    2.1558    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -0.1078    1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -0.2290    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.4844   -1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277    1.9740   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3767    0.4014   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559   -0.7467    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.2450    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508   -3.2195    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8202    0.2351   -1.2610 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  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
  8 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 16 30  1  0
M  END

HEADER    PROTEIN                                 17-APR-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: [NO NAME]                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-12         0                                  
HETATM    1  O   UNK     0       3.080   0.309   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   0.309   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       5.748  -4.311   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       4.414  -2.001   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       7.081  -2.001   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.748   0.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   1.643   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.518   1.643   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -0.461   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -0.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.437   1.643   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748   2.977   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.058   1.643   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -2.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.518   4.311   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.828   2.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.058   4.311   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.828   5.644   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   14                                                            
CONECT    4    9   14                                                       
CONECT    5   10   14                                                       
CONECT    6    7    8    9   10                                             
CONECT    7    6   11                                                       
CONECT    8    6   12   13                                                  
CONECT    9    1    4    6                                                  
CONECT   10    2    5    6                                                  
CONECT   11    7                                                            
CONECT   12    8   15                                                       
CONECT   13    8   16                                                       
CONECT   14    3    4    5                                                  
CONECT   15   12   17                                                       
CONECT   16   13   17                                                       
CONECT   17   15   16   18                                                  
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0060537
HETATM    1  C1  UNL     1      -1.024   1.737   1.306  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.149   0.229   1.244  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.681  -0.295  -0.116  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.714   0.087  -0.294  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.231   0.969  -1.183  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.583   1.260  -1.255  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.462   0.638  -0.396  1.00  0.00           C  
HETATM    8  O1  UNL     1       4.804   0.957  -0.502  1.00  0.00           O  
HETATM    9  C8  UNL     1       2.960  -0.260   0.514  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.624  -0.540   0.576  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.814  -1.799  -0.012  1.00  0.00           C  
HETATM   12  O2  UNL     1       0.130  -2.589  -0.117  1.00  0.00           O  
HETATM   13  N1  UNL     1      -2.129  -2.304   0.220  1.00  0.00           N  
HETATM   14  C11 UNL     1      -3.262  -1.571  -0.231  1.00  0.00           C  
HETATM   15  O3  UNL     1      -4.436  -2.004  -0.034  1.00  0.00           O  
HETATM   16  N2  UNL     1      -3.008  -0.346  -0.904  1.00  0.00           N  
HETATM   17  C12 UNL     1      -1.650   0.123  -1.113  1.00  0.00           C  
HETATM   18  O4  UNL     1      -1.493   0.828  -2.129  1.00  0.00           O  
HETATM   19  H1  UNL     1      -2.045   2.142   1.453  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.424   2.035   2.193  1.00  0.00           H  
HETATM   21  H3  UNL     1      -0.518   2.156   0.423  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.179  -0.108   1.391  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.477  -0.229   1.993  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.597   1.484  -1.868  1.00  0.00           H  
HETATM   25  H7  UNL     1       2.928   1.974  -1.987  1.00  0.00           H  
HETATM   26  H8  UNL     1       5.377   0.401  -1.134  1.00  0.00           H  
HETATM   27  H9  UNL     1       3.656  -0.747   1.187  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.295  -1.245   1.315  1.00  0.00           H  
HETATM   29  H11 UNL     1      -2.251  -3.220   0.724  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.820   0.235  -1.261  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    7   25
CONECT    7    8    9
CONECT    8   26
CONECT    9   10   10   27
CONECT   10   28
CONECT   11   12   12   13
CONECT   13   14   29
CONECT   14   15   15   16
CONECT   16   17   30
CONECT   17   18   18
END

HMDB0060537
     RDKit          3D
p-Hydroxyphenobarbital
 30 31  0  0  0  0  0  0  0  0999 V2000
   -1.0240    1.7365    1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1492    0.2294    1.2443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6805   -0.2951   -0.1161 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    0.0867   -0.2940 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2312    0.9695   -1.1827 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5825    1.2598   -1.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4623    0.6382   -0.3961 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8035    0.9570   -0.5019 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9599   -0.2603    0.5136 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6244   -0.5395    0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144   -1.7994   -0.0125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1303   -2.5892   -0.1171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1287   -2.3038    0.2197 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2618   -1.5711   -0.2313 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4358   -2.0042   -0.0344 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0085   -0.3458   -0.9042 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6498    0.1233   -1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4929    0.8281   -2.1292 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0453    2.1421    1.4527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4242    2.0349    2.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176    2.1558    0.4228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1791   -0.1078    1.3907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4775   -0.2290    1.9931 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5969    1.4844   -1.8685 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9277    1.9740   -1.9874 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3767    0.4014   -1.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6559   -0.7467    1.1869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.2450    1.3155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508   -3.2195    0.7242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8202    0.2351   -1.2610 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  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
  8 26  1  0
  9 27  1  0
 10 28  1  0
 13 29  1  0
 16 30  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
p-Hydroxy-phenobarbitone	HMDB
Para-hydroxyphenobarbital	HMDB
p-Hydroxy-PB	HMDB

Chemical Formula

C₁₂H₁₂N₂O₄

Average Molecular Weight

248.2347

Monoisotopic Molecular Weight

248.079706882

IUPAC Name

5-ethyl-5-(4-hydroxyphenyl)-1,3-diazinane-2,4,6-trione

Traditional Name

5-ethyl-5-(4-hydroxyphenyl)-1,3-diazinane-2,4,6-trione

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H12N2O4/c1-2-12(7-3-5-8(15)6-4-7)9(16)13-11(18)14-10(12)17/h3-6,15H,2H2,1H3,(H2,13,14,16,17,18)

InChI Key

IEPXMKJNWPXDBP-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
1-hydroxy-2-unsubstituted benzenoid
N-acyl urea
Phenol
Ureide
Monocyclic benzene moiety
1,3-diazinane
Benzenoid
Dicarboximide
Urea
Carbonic acid derivative
Carboxylic acid derivative
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060537)

Organ

Kidney (HMDB: HMDB0060537)
Liver (HMDB: HMDB0060537)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060537)

Cellular substructure

Cytoplasm (HMDB: HMDB0060537)

Source

Endogenous

Endogenous (HMDB: HMDB0060537)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.98 g/L	ALOGPS
logP	0.85	ALOGPS
logP	1.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	8.12	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	95.5 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.73 m³·mol⁻¹	ChemAxon
Polarizability	23.61 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]+	156.718	31661259
DarkChem	[M-H]-	152.914	31661259
DeepCCS	[M+H]+	168.697	30932474
DeepCCS	[M-H]-	166.339	30932474
DeepCCS	[M-2H]-	199.225	30932474
DeepCCS	[M+Na]+	174.79	30932474
AllCCS	[M+H]+	155.6	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	159.2	32859911
AllCCS	[M+Na]+	160.2	32859911
AllCCS	[M-H]-	156.5	32859911
AllCCS	[M+Na-2H]-	156.4	32859911
AllCCS	[M+HCOO]-	156.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
p-Hydroxyphenobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CC=C(O)C=C1	4069.1	Standard polar	33892256
p-Hydroxyphenobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CC=C(O)C=C1	2398.3	Standard non polar	33892256
p-Hydroxyphenobarbital	CCC1(C(=O)NC(=O)NC1=O)C1=CC=C(O)C=C1	2381.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
p-Hydroxyphenobarbital,1TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)NC(=O)NC1=O	2265.0	Semi standard non polar	33892256
p-Hydroxyphenobarbital,1TMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2096.0	Semi standard non polar	33892256
p-Hydroxyphenobarbital,2TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2177.7	Semi standard non polar	33892256
p-Hydroxyphenobarbital,2TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	2366.2	Standard non polar	33892256
p-Hydroxyphenobarbital,2TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)NC(=O)N([Si](C)(C)C)C1=O	3188.8	Standard polar	33892256
p-Hydroxyphenobarbital,2TMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2008.6	Semi standard non polar	33892256
p-Hydroxyphenobarbital,2TMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2342.9	Standard non polar	33892256
p-Hydroxyphenobarbital,2TMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2910.3	Standard polar	33892256
p-Hydroxyphenobarbital,3TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2119.1	Semi standard non polar	33892256
p-Hydroxyphenobarbital,3TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2369.2	Standard non polar	33892256
p-Hydroxyphenobarbital,3TMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C)C=C2)C(=O)N([Si](C)(C)C)C(=O)N([Si](C)(C)C)C1=O	2679.7	Standard polar	33892256
p-Hydroxyphenobarbital,1TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)NC(=O)NC1=O	2476.3	Semi standard non polar	33892256
p-Hydroxyphenobarbital,1TBDMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2371.7	Semi standard non polar	33892256
p-Hydroxyphenobarbital,2TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2621.3	Semi standard non polar	33892256
p-Hydroxyphenobarbital,2TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	2822.7	Standard non polar	33892256
p-Hydroxyphenobarbital,2TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)NC(=O)N([Si](C)(C)C(C)(C)C)C1=O	3265.2	Standard polar	33892256
p-Hydroxyphenobarbital,2TBDMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2502.9	Semi standard non polar	33892256
p-Hydroxyphenobarbital,2TBDMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2798.2	Standard non polar	33892256
p-Hydroxyphenobarbital,2TBDMS,isomer #2	CCC1(C2=CC=C(O)C=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2996.8	Standard polar	33892256
p-Hydroxyphenobarbital,3TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2804.4	Semi standard non polar	33892256
p-Hydroxyphenobarbital,3TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	3020.4	Standard non polar	33892256
p-Hydroxyphenobarbital,3TBDMS,isomer #1	CCC1(C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2)C(=O)N([Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2924.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxyphenobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-1790000000-04c54f3388973824b101	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxyphenobarbital GC-MS (1 TMS) - 70eV, Positive	splash10-062c-3192000000-fded03ae24218c64c8b9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxyphenobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - p-Hydroxyphenobarbital 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 - p-Hydroxyphenobarbital 10V, Positive-QTOF	splash10-0002-0190000000-d98a0398c95d1c6f4a81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 20V, Positive-QTOF	splash10-004i-0920000000-df72e42c0fcb2c6c2e8b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 40V, Positive-QTOF	splash10-00lr-5900000000-3e45278a0a390b730aca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 10V, Negative-QTOF	splash10-0f6y-6090000000-53548f008a7f16a0dbb1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 20V, Negative-QTOF	splash10-0006-9520000000-93e86efebaa6dbde584c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 40V, Negative-QTOF	splash10-0006-9700000000-3b7b8b4679162d3124d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 10V, Positive-QTOF	splash10-0002-0190000000-101892e432ef202fd145	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 20V, Positive-QTOF	splash10-001r-0920000000-71b52ae7a75b98e8ec39	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 40V, Positive-QTOF	splash10-05o0-3920000000-036b204c1ba93d5c8ea6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 10V, Negative-QTOF	splash10-002f-9800000000-a91d5d488215830432d6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 20V, Negative-QTOF	splash10-0006-9100000000-8d8b98292f3e4a2569d9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - p-Hydroxyphenobarbital 40V, Negative-QTOF	splash10-0006-9100000000-d73a2a83b00524019350	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9785

PDB ID

Not Available

ChEBI ID

Not Available

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

Showing metabocard for p-Hydroxyphenobarbital (HMDB0060537)

MOL for HMDB0060537 (p-Hydroxyphenobarbital)

3D MOL for HMDB0060537 (p-Hydroxyphenobarbital)

3D SDF for HMDB0060537 (p-Hydroxyphenobarbital)

3D-SDF for HMDB0060537 (p-Hydroxyphenobarbital)

PDB for HMDB0060537 (p-Hydroxyphenobarbital)

3D PDB for HMDB0060537 (p-Hydroxyphenobarbital)

SMILES for HMDB0060537 (p-Hydroxyphenobarbital)

INCHI for HMDB0060537 (p-Hydroxyphenobarbital)

Structure for HMDB0060537 (p-Hydroxyphenobarbital)

3D Structure for HMDB0060537 (p-Hydroxyphenobarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra