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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:49 UTC

HMDB ID

HMDB0014987

Secondary Accession Numbers

HMDB14987

Metabolite Identification

Common Name

Methylphenobarbital

Description

Methylphenobarbital, also known as mebaral or mephobarbitone, 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. It is the N-methylated analogue of phenobarbital and has similar indications, therapeutic value, and tolerability.1935 – Mebaral was introduced by Winthrop Pharmaceuticals.2001 – Methylphenobarbital discontinued in the UK.2003 – Mebaral was acquired by Ovation Pharmaceuticals (a specialty pharmaceutical company that acquired under-promoted branded pharmaceutical products).2009 – Ovation was acquired by Lundbeck, which now markets Mebaral.2012 – Lundbeck announced that they were abandoning the product in the US as of January 6, 2012. Methylphenobarbital is a drug which is used for the relief of anxiety, tension, and apprehension, also used as an anticonvulsant for the treatment of epilepsy. The last available tablets bore an expiration date of March 31, 2012, and the drug will no longer be available in the US when supplies are depleted. Methylphenobarbital is a very weakly acidic compound (based on its pKa). The stated reason was because "the company thoroughly evaluated all avenues for keeping Mebaral available to patients, but ultimately concluded that no matter what steps they [i.e. Lundbeck] took, patients would be forced to transition to a new therapy."The company further stated in a letter on its website that under the FDA's Unapproved Drugs Initiative, FDA is no longer willing to allow the drug to be grandfathered. Methylphenobarbital is a potentially toxic compound. A new drug application would have needed to have been submitted to gain marketing approval, which would have taken an estimated five years, during which time patients would be required to change their therapies in any case. Symptoms of overdose of mephobarbital include confusion, decrease in or loss of reflexes, somnolence, fever, irritability, hypothermia, poor judgment, shortness of breath or slow/troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness.

Structure

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

HMDB0014987
     RDKit          3D
Methylphenobarbital
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.4007    2.9672   -0.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    1.8833   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.6401    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -0.3900    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -0.3881   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2375   -1.3981   -0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -2.4509    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0064   -2.4601    0.9986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -1.4577    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2291    1.0723    1.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4612    1.9488    1.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3658    0.5080    1.9989 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3350   -0.2075    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3235   -0.6913    1.8534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -0.3780   -0.1249 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1977   -1.1151   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526    0.1805   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.2905   -2.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0747    3.9490   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936    2.9573    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    2.7485   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548    2.2711   -0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8676    1.6238   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422    0.4057   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739   -1.3418   -1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8800   -3.1998    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8943   -3.2828    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2224   -1.5051    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5035    0.6182    3.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1447   -0.5013   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -2.1080   -0.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8897   -1.1884   -1.9115 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
  8  9  2  0
  3 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  3  1  0
  9  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
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  END

849
  Mrv0541 02231215032D          

 18 19  0  0  1  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   -1.4842    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
    1.6500   -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
  1  9  2  0  0  0  0
  2 10  2  0  0  0  0
  3 12  2  0  0  0  0
  4  9  1  0  0  0  0
  4 12  1  0  0  0  0
  4 15  1  0  0  0  0
  5 10  1  0  0  0  0
  5 12  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 13  2  0  0  0  0
  8 14  1  0  0  0  0
 13 16  1  0  0  0  0
 14 17  2  0  0  0  0
 16 18  2  0  0  0  0
 17 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014987

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)

> <INCHI_KEY>
ALARQZQTBTVLJV-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O3

> <MOLECULAR_WEIGHT>
246.2619

> <EXACT_MASS>
246.100442324

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.61609168147472

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
1.6300061936666659

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.399004668484812

> <JCHEM_POLAR_SURFACE_AREA>
66.48

> <JCHEM_REFRACTIVITY>
64.643

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylphenobarbital

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014987
     RDKit          3D
Methylphenobarbital
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.4007    2.9672   -0.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    1.8833   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.6401    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -0.3900    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -0.3881   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2375   -1.3981   -0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -2.4509    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0064   -2.4601    0.9986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -1.4577    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2291    1.0723    1.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4612    1.9488    1.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3658    0.5080    1.9989 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3350   -0.2075    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3235   -0.6913    1.8534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -0.3780   -0.1249 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1977   -1.1151   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526    0.1805   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.2905   -2.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0747    3.9490   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936    2.9573    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    2.7485   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548    2.2711   -0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8676    1.6238   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422    0.4057   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739   -1.3418   -1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8800   -3.1998    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8943   -3.2828    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2224   -1.5051    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5035    0.6182    3.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1447   -0.5013   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -2.1080   -0.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8897   -1.1884   -1.9115 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
  8  9  2  0
  3 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  3  1  0
  9  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
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 849                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-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  -2.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.748   2.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.058   1.643   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080  -2.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.518   4.311   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.828   2.977   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.058   4.311   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   12                                                            
CONECT    4    9   12   15                                                  
CONECT    5   10   12                                                       
CONECT    6    7    8    9   10                                             
CONECT    7    6   11                                                       
CONECT    8    6   13   14                                                  
CONECT    9    1    4    6                                                  
CONECT   10    2    5    6                                                  
CONECT   11    7                                                            
CONECT   12    3    4    5                                                  
CONECT   13    8   16                                                       
CONECT   14    8   17                                                       
CONECT   15    4                                                            
CONECT   16   13   18                                                       
CONECT   17   14   18                                                       
CONECT   18   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0014987
HETATM    1  C1  UNL     1       0.401   2.967  -0.738  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.681   1.883  -0.720  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.142   0.640   0.005  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.180  -0.390   0.025  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.293  -0.388  -0.800  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.238  -1.398  -0.727  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.104  -2.451   0.179  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.006  -2.460   0.999  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.070  -1.458   0.924  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.229   1.072   1.369  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.461   1.949   1.990  1.00  0.00           O  
HETATM   12  N1  UNL     1       1.366   0.508   1.999  1.00  0.00           N  
HETATM   13  C11 UNL     1       2.335  -0.207   1.270  1.00  0.00           C  
HETATM   14  O2  UNL     1       3.324  -0.691   1.853  1.00  0.00           O  
HETATM   15  N2  UNL     1       2.188  -0.378  -0.125  1.00  0.00           N  
HETATM   16  C12 UNL     1       3.198  -1.115  -0.840  1.00  0.00           C  
HETATM   17  C13 UNL     1       1.053   0.181  -0.779  1.00  0.00           C  
HETATM   18  O3  UNL     1       1.052   0.290  -2.039  1.00  0.00           O  
HETATM   19  H1  UNL     1      -0.075   3.949  -0.931  1.00  0.00           H  
HETATM   20  H2  UNL     1       0.994   2.957   0.206  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.096   2.749  -1.575  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.555   2.271  -0.195  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.868   1.624  -1.792  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.442   0.406  -1.517  1.00  0.00           H  
HETATM   25  H7  UNL     1      -4.074  -1.342  -1.389  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.880  -3.200   0.177  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.894  -3.283   1.712  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.222  -1.505   1.590  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.503   0.618   3.040  1.00  0.00           H  
HETATM   30  H12 UNL     1       4.145  -0.501  -0.866  1.00  0.00           H  
HETATM   31  H13 UNL     1       3.413  -2.108  -0.392  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.890  -1.188  -1.911  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   22   23
CONECT    3    4   10   17
CONECT    4    5    5    9
CONECT    5    6   24
CONECT    6    7    7   25
CONECT    7    8   26
CONECT    8    9    9   27
CONECT    9   28
CONECT   10   11   11   12
CONECT   12   13   29
CONECT   13   14   14   15
CONECT   15   16   17
CONECT   16   30   31   32
CONECT   17   18   18
END

HMDB0014987
     RDKit          3D
Methylphenobarbital
 32 33  0  0  0  0  0  0  0  0999 V2000
    0.4007    2.9672   -0.7383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6809    1.8833   -0.7205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1423    0.6401    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1798   -0.3900    0.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2926   -0.3881   -0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2375   -1.3981   -0.7265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1041   -2.4509    0.1785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0064   -2.4601    0.9986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -1.4577    0.9240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2291    1.0723    1.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4612    1.9488    1.9896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3658    0.5080    1.9989 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3350   -0.2075    1.2701 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3235   -0.6913    1.8534 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -0.3780   -0.1249 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1977   -1.1151   -0.8401 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0526    0.1805   -0.7787 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0522    0.2905   -2.0389 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0747    3.9490   -0.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9936    2.9573    0.2063 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0961    2.7485   -1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5548    2.2711   -0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8676    1.6238   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4422    0.4057   -1.5173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0739   -1.3418   -1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8800   -3.1998    0.1774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8943   -3.2828    1.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2224   -1.5051    1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5035    0.6182    3.0397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1447   -0.5013   -0.8658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4132   -2.1080   -0.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8897   -1.1884   -1.9115 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
  8  9  2  0
  3 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17  3  1  0
  9  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
  7 26  1  0
  8 27  1  0
  9 28  1  0
 12 29  1  0
 16 30  1  0
 16 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Methylphenobarbital	ChEBI
5-Ethyl-1-methyl-5-phenyl-2,4,6(1H,3H,5H)-pyrimidinetrione	ChEBI
5-Ethyl-1-methyl-5-phenyl-pyrimidine-2,4,6-trione	ChEBI
5-Ethyl-1-methyl-5-phenylbarbituric acid	ChEBI
Mebaral	ChEBI
Mephobarbitone	ChEBI
Methylphenobarbitalum	ChEBI
Metilfenobarbital	ChEBI
N-Methylphenobarbital	ChEBI
5-Ethyl-1-methyl-5-phenylbarbitate	Generator
5-Ethyl-1-methyl-5-phenylbarbitic acid	Generator
Mephobarbital	HMDB
Methyl phenobarbitone	HMDB
Methylphenobarbitonum	HMDB
Methylphenolbarbital	HMDB
Methylphenylbarbituric acid	HMDB
Metilfenobarbitale	HMDB
N-Ethylmethylphenylbarbituric acid	HMDB
N-Methylethylphenylbarbituric acid	HMDB
N-Methylphenolbarbitol	HMDB
Methylphenobarbitone	HMDB
Sanofi synthelabo brand OF mephobarbital	HMDB
Prominal	HMDB
Sanofi brand OF mephobarbital	HMDB
Methylphenobarbital	ChEBI

Chemical Formula

C₁₃H₁₄N₂O₃

Average Molecular Weight

246.2619

Monoisotopic Molecular Weight

246.100442324

IUPAC Name

5-ethyl-1-methyl-5-phenyl-1,3-diazinane-2,4,6-trione

Traditional Name

methylphenobarbital

CAS Registry Number

115-38-8

SMILES

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

InChI Identifier

InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18)

InChI Key

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

barbiturates (CHEBI:6758 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014987)

Source

Exogenous

Exogenous (HMDB: HMDB0014987)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	176 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.71 g/L	Not Available
LogP	1.84	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.71 g/L	ALOGPS
logP	1.95	ALOGPS
logP	1.63	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.64 m³·mol⁻¹	ChemAxon
Polarizability	24.62 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]+	159.288	31661259
DarkChem	[M-H]-	154.478	31661259
DeepCCS	[M+H]+	161.587	30932474
DeepCCS	[M-H]-	159.229	30932474
DeepCCS	[M-2H]-	192.115	30932474
DeepCCS	[M+Na]+	167.681	30932474
AllCCS	[M+H]+	155.4	32859911
AllCCS	[M+H-H2O]+	151.5	32859911
AllCCS	[M+NH4]+	159.0	32859911
AllCCS	[M+Na]+	160.1	32859911
AllCCS	[M-H]-	158.3	32859911
AllCCS	[M+Na-2H]-	158.3	32859911
AllCCS	[M+HCOO]-	158.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methylphenobarbital	CCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C1	3310.9	Standard polar	33892256
Methylphenobarbital	CCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C1	1858.9	Standard non polar	33892256
Methylphenobarbital	CCC1(C(=O)NC(=O)N(C)C1=O)C1=CC=CC=C1	1892.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methylphenobarbital,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O	1833.0	Semi standard non polar	33892256
Methylphenobarbital,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O	2057.9	Standard non polar	33892256
Methylphenobarbital,1TMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C)C1=O	2651.2	Standard polar	33892256
Methylphenobarbital,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2103.4	Semi standard non polar	33892256
Methylphenobarbital,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2306.4	Standard non polar	33892256
Methylphenobarbital,1TBDMS,isomer #1	CCC1(C2=CC=CC=C2)C(=O)N(C)C(=O)N([Si](C)(C)C(C)(C)C)C1=O	2732.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Methylphenobarbital EI-B (Non-derivatized)	splash10-014i-7890000000-2901bd43c9c369accc5e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Methylphenobarbital EI-B (Non-derivatized)	splash10-014i-7890000000-2901bd43c9c369accc5e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylphenobarbital GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1960000000-03c5912fae96e516bc08	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylphenobarbital GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methylphenobarbital 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 - Methylphenobarbital 10V, Positive-QTOF	splash10-0002-0090000000-5efc4c40b94c015f15d1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 20V, Positive-QTOF	splash10-00os-0930000000-00256f4ed6f9589accfb	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 40V, Positive-QTOF	splash10-014l-8900000000-852f79784f92a016b588	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 10V, Negative-QTOF	splash10-0f6t-4190000000-7afe5dafc1ac46950ae9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 20V, Negative-QTOF	splash10-05fr-5900000000-adbe9ddcf8d5310392d5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 40V, Negative-QTOF	splash10-0006-9400000000-e18ddad976005362cdce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 10V, Positive-QTOF	splash10-0002-0090000000-c3b5328faa9ccd492274	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 20V, Positive-QTOF	splash10-014i-1940000000-83b4742c95ac40de815f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 40V, Positive-QTOF	splash10-00kf-9700000000-70a6a2b92d607f53d798	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 10V, Negative-QTOF	splash10-0002-0090000000-bd60669c03ea828062a5	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 20V, Negative-QTOF	splash10-0006-9320000000-d8726243263b97488adb	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methylphenobarbital 40V, Negative-QTOF	splash10-0006-9300000000-fb4279919738a6bc3b7c	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 DB00849	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00849	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00849

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7972

KEGG Compound ID

C07829

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Methylphenobarbital

METLIN ID

Not Available

PubChem Compound

8271

PDB ID

Not Available

ChEBI ID

6758

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. Cytochrome P450 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2B6

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:: CYP2B6
Uniprot ID:: P20813
Molecular weight:: 56277.81

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. 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

4. 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

5. 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 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]
Roden WH, Peugh LD, Jansen LA: Altered GABA(A) receptor subunit expression and pharmacology in human Angelman syndrome cortex. Neurosci Lett. 2010 Oct 15;483(3):167-72. doi: 10.1016/j.neulet.2010.08.001. Epub 2010 Aug 6. [PubMed:20692323 ]

Enzyme Details

6. 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 ]
Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]

Enzyme Details

7. 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 ]
Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]

Enzyme Details

8. 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 ]
Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]

Enzyme Details

9. 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 ]
Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]

Enzyme Details

10. 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 ]
Olsen RW, Li GD: GABA(A) receptors as molecular targets of general anesthetics: identification of binding sites provides clues to allosteric modulation. Can J Anaesth. 2011 Feb;58(2):206-15. doi: 10.1007/s12630-010-9429-7. Epub 2010 Dec 31. [PubMed:21194017 ]

Showing metabocard for Methylphenobarbital (HMDB0014987)

MOL for HMDB0014987 (Methylphenobarbital)

3D MOL for HMDB0014987 (Methylphenobarbital)

3D SDF for HMDB0014987 (Methylphenobarbital)

3D-SDF for HMDB0014987 (Methylphenobarbital)

PDB for HMDB0014987 (Methylphenobarbital)

3D PDB for HMDB0014987 (Methylphenobarbital)

SMILES for HMDB0014987 (Methylphenobarbital)

INCHI for HMDB0014987 (Methylphenobarbital)

Structure for HMDB0014987 (Methylphenobarbital)

3D Structure for HMDB0014987 (Methylphenobarbital)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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