Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:51 UTC

HMDB ID

HMDB0015084

Secondary Accession Numbers

HMDB15084

Metabolite Identification

Common Name

Felbamate

Description

Felbamate, also known as felbamatum or felbatol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Felbamate is a drug which is used for use only in those patients who respond inadequately to alternative treatments and whose epilepsy is so severe that a substantial risk of aplastic anemia and/or liver failure is deemed acceptable in light of the benefits conferred by its use. Felbamate is a very weakly acidic compound (based on its pKa). Within humans, felbamate participates in a number of enzymatic reactions. In particular, felbamate can be converted into 2-hydroxyfelbamate; which is mediated by the enzymes cytochrome P450 2E1 and cytochrome P450 3A4. In addition, felbamate can be converted into p-hydroxyfelbamate; which is mediated by the enzymes cytochrome P450 3A4 and cytochrome P450 2E1. In humans, felbamate is involved in felbamate metabolism pathway. Felbamate is a potentially toxic compound. The bis(carbamate ester) of 2-phenylpropane-1,3-diol.

Structure

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

HMDB0015084
     RDKit          3D
Felbamate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.6424    0.1372   -0.4464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612    0.9343   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059    2.1445   -0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    0.3937   -0.7621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    1.1159   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972    0.2349   -1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4081    1.0232   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    1.4884    0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180    2.2332    0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478    2.7020    1.8398 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    2.5147   -0.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -0.9657   -0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4845   -0.9643    0.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -2.1495    1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -3.3784    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967   -3.3728   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2376   -2.1944   -0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5930    0.5928   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6236   -0.8968   -0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    1.6069    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1292    1.9269   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714   -0.0261   -2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2285    0.3575   -1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    1.8529   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    3.1363    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8854    2.6252    2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -0.0358    1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103   -2.1608    2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335   -4.3105    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -4.3179   -0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0730   -2.2476   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

949
  Mrv0541 02231215072D          

 17 17  0  0  0  0            999 V2000
    3.0791    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.1096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.3472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.3472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.1279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.9529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    0.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  1  0  0  0  0
  1 16  1  0  0  0  0
  2 10  1  0  0  0  0
  2 17  1  0  0  0  0
  3 16  2  0  0  0  0
  4 17  2  0  0  0  0
  5 16  1  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
 11 13  1  0  0  0  0
 12 14  2  0  0  0  0
 13 15  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015084

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)OCC(COC(N)=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)

> <INCHI_KEY>
WKGXYQFOCVYPAC-UHFFFAOYSA-N

> <FORMULA>
C11H14N2O4

> <MOLECULAR_WEIGHT>
238.2399

> <EXACT_MASS>
238.095356946

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.517405044317194

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(carbamoyloxy)-2-phenylpropyl carbamate

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
0.6795679436666664

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.460661108821839

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.982561981985281

> <JCHEM_POLAR_SURFACE_AREA>
104.64

> <JCHEM_REFRACTIVITY>
59.58680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
felbamate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015084
     RDKit          3D
Felbamate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.6424    0.1372   -0.4464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612    0.9343   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059    2.1445   -0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    0.3937   -0.7621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    1.1159   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972    0.2349   -1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4081    1.0232   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    1.4884    0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180    2.2332    0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478    2.7020    1.8398 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    2.5147   -0.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -0.9657   -0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4845   -0.9643    0.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -2.1495    1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -3.3784    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967   -3.3728   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2376   -2.1944   -0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5930    0.5928   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6236   -0.8968   -0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    1.6069    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1292    1.9269   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714   -0.0261   -2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2285    0.3575   -1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    1.8529   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    3.1363    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8854    2.6252    2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -0.0358    1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103   -2.1608    2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335   -4.3105    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -4.3179   -0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0730   -2.2476   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 949                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748   2.071   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       8.415   2.071   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080   2.071   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      11.082   2.071   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       4.414   4.381   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       9.748   4.381   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.081  -0.239   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -1.779   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.748   0.531   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   0.531   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -2.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.748  -2.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -4.089   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.748  -4.089   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.081  -4.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.414   2.841   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748   2.841   0.000  0.00  0.00           C+0
CONECT    1    9   16                                                       
CONECT    2   10   17                                                       
CONECT    3   16                                                            
CONECT    4   17                                                            
CONECT    5   16                                                            
CONECT    6   17                                                            
CONECT    7    8    9   10                                                  
CONECT    8    7   11   12                                                  
CONECT    9    1    7                                                       
CONECT   10    2    7                                                       
CONECT   11    8   13                                                       
CONECT   12    8   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   15                                                       
CONECT   15   13   14                                                       
CONECT   16    1    3    5                                                  
CONECT   17    2    4    6                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0015084
HETATM    1  N1  UNL     1      -4.642   0.137  -0.446  1.00  0.00           N  
HETATM    2  C1  UNL     1      -3.461   0.934  -0.414  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.506   2.144  -0.068  1.00  0.00           O  
HETATM    4  O2  UNL     1      -2.241   0.394  -0.762  1.00  0.00           O  
HETATM    5  C2  UNL     1      -1.039   1.116  -0.754  1.00  0.00           C  
HETATM    6  C3  UNL     1       0.097   0.235  -1.184  1.00  0.00           C  
HETATM    7  C4  UNL     1       1.408   1.023  -1.175  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.633   1.488   0.143  1.00  0.00           O  
HETATM    9  C5  UNL     1       2.718   2.233   0.519  1.00  0.00           C  
HETATM   10  N2  UNL     1       2.948   2.702   1.840  1.00  0.00           N  
HETATM   11  O4  UNL     1       3.568   2.515  -0.391  1.00  0.00           O  
HETATM   12  C6  UNL     1       0.277  -0.966  -0.367  1.00  0.00           C  
HETATM   13  C7  UNL     1       0.485  -0.964   0.987  1.00  0.00           C  
HETATM   14  C8  UNL     1       0.643  -2.150   1.663  1.00  0.00           C  
HETATM   15  C9  UNL     1       0.606  -3.378   1.049  1.00  0.00           C  
HETATM   16  C10 UNL     1       0.397  -3.373  -0.316  1.00  0.00           C  
HETATM   17  C11 UNL     1       0.238  -2.194  -0.998  1.00  0.00           C  
HETATM   18  H1  UNL     1      -5.593   0.593  -0.549  1.00  0.00           H  
HETATM   19  H2  UNL     1      -4.624  -0.897  -0.373  1.00  0.00           H  
HETATM   20  H3  UNL     1      -0.878   1.607   0.217  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.129   1.927  -1.507  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.071  -0.026  -2.246  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.229   0.357  -1.515  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.366   1.853  -1.916  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.189   3.136   2.402  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.885   2.625   2.288  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.522  -0.036   1.518  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.810  -2.161   2.751  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.733  -4.311   1.599  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.359  -4.318  -0.851  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.073  -2.248  -2.088  1.00  0.00           H  
CONECT    1    2   18   19
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   20   21
CONECT    6    7   12   22
CONECT    7    8   23   24
CONECT    8    9
CONECT    9   10   11   11
CONECT   10   25   26
CONECT   12   13   13   17
CONECT   13   14   27
CONECT   14   15   15   28
CONECT   15   16   29
CONECT   16   17   17   30
CONECT   17   31
END

HMDB0015084
     RDKit          3D
Felbamate
 31 31  0  0  0  0  0  0  0  0999 V2000
   -4.6424    0.1372   -0.4464 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612    0.9343   -0.4140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5059    2.1445   -0.0685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2406    0.3937   -0.7621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0389    1.1159   -0.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0972    0.2349   -1.1836 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4081    1.0232   -1.1746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6334    1.4884    0.1428 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7180    2.2332    0.5193 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9478    2.7020    1.8398 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    2.5147   -0.3910 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2772   -0.9657   -0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4845   -0.9643    0.9865 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6430   -2.1495    1.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6061   -3.3784    1.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3967   -3.3728   -0.3157 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2376   -2.1944   -0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5930    0.5928   -0.5491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6236   -0.8968   -0.3728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8780    1.6069    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1292    1.9269   -1.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0714   -0.0261   -2.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2285    0.3575   -1.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3660    1.8529   -1.9156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    3.1363    2.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8854    2.6252    2.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5224   -0.0358    1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8103   -2.1608    2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7335   -4.3105    1.5988 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3586   -4.3179   -0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0730   -2.2476   -2.0885 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  6 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Phenyl-1,3-propanediol dicarbamate	ChEBI
Carbamic acid 2-phenyltrimethylene ester	ChEBI
Carbamic acid 3-carbamoyloxy-2-phenyl-propyl ester	ChEBI
Felbamato	ChEBI
Felbamatum	ChEBI
Felbatol	Kegg
2-Phenyl-1,3-propanediol dicarbamic acid	Generator
Carbamate 2-phenyltrimethylene ester	Generator
Carbamate 3-carbamoyloxy-2-phenyl-propyl ester	Generator
Felbamic acid	Generator
Felbamyl	HMDB
Wallace brand 1 OF felbamate	HMDB
Taloxa	HMDB
Wallace brand 2 OF felbamate	HMDB
(3-Carbamoyloxy-2-phenyl-propyl) carbamate	HMDB
2 Phenyl 1,3 propanediol dicarbamate	HMDB

Chemical Formula

C₁₁H₁₄N₂O₄

Average Molecular Weight

238.2399

Monoisotopic Molecular Weight

238.095356946

IUPAC Name

3-(carbamoyloxy)-2-phenylpropyl carbamate

Traditional Name

felbamate

CAS Registry Number

25451-15-4

SMILES

NC(=O)OCC(COC(N)=O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C11H14N2O4/c12-10(14)16-6-9(7-17-11(13)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H2,12,14)(H2,13,15)

InChI Key

WKGXYQFOCVYPAC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents

Substituents

Monocyclic benzene moiety
Carbamic acid ester
Carbonic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

carbamate ester (CHEBI:4995 )

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: HMDB0015084)

Source

Exogenous

Exogenous (HMDB: HMDB0015084)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Felbamate Metabolism Pathway (PathBank: SMP0000633)

Role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Anticonvulsant (HMDB: HMDB0015084)

Neuroprotective agent (HMDB: HMDB0015084)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	151.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.74 g/L	Not Available
LogP	0.3	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.74 g/L	ALOGPS
logP	0.56	ALOGPS
logP	0.68	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	14.98	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	104.64 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	59.59 m³·mol⁻¹	ChemAxon
Polarizability	23.52 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]+	154.842	31661259
DarkChem	[M-H]-	147.492	31661259
DeepCCS	[M+H]+	157.92	30932474
DeepCCS	[M-H]-	155.536	30932474
DeepCCS	[M-2H]-	189.001	30932474
DeepCCS	[M+Na]+	163.987	30932474
AllCCS	[M+H]+	151.8	32859911
AllCCS	[M+H-H2O]+	148.1	32859911
AllCCS	[M+NH4]+	155.2	32859911
AllCCS	[M+Na]+	156.2	32859911
AllCCS	[M-H]-	152.0	32859911
AllCCS	[M+Na-2H]-	152.3	32859911
AllCCS	[M+HCOO]-	152.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.93 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2449 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	213.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	922.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	255.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	102.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	280.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	306.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	719.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	724.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	187.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	807.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	185.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	244.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	404.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	385.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	219.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Felbamate	NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	3284.0	Standard polar	33892256
Felbamate	NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	2035.4	Standard non polar	33892256
Felbamate	NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	2198.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Felbamate,1TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	2173.1	Semi standard non polar	33892256
Felbamate,1TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	2111.9	Standard non polar	33892256
Felbamate,1TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	3361.7	Standard polar	33892256
Felbamate,2TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(=O)N[Si](C)(C)C)C1=CC=CC=C1	2295.8	Semi standard non polar	33892256
Felbamate,2TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(=O)N[Si](C)(C)C)C1=CC=CC=C1	2236.0	Standard non polar	33892256
Felbamate,2TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(=O)N[Si](C)(C)C)C1=CC=CC=C1	2882.2	Standard polar	33892256
Felbamate,2TMS,isomer #2	C[Si](C)(C)N(C(=O)OCC(COC(N)=O)C1=CC=CC=C1)[Si](C)(C)C	2229.4	Semi standard non polar	33892256
Felbamate,2TMS,isomer #2	C[Si](C)(C)N(C(=O)OCC(COC(N)=O)C1=CC=CC=C1)[Si](C)(C)C	2230.7	Standard non polar	33892256
Felbamate,2TMS,isomer #2	C[Si](C)(C)N(C(=O)OCC(COC(N)=O)C1=CC=CC=C1)[Si](C)(C)C	3219.0	Standard polar	33892256
Felbamate,3TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2308.0	Semi standard non polar	33892256
Felbamate,3TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2327.3	Standard non polar	33892256
Felbamate,3TMS,isomer #1	C[Si](C)(C)NC(=O)OCC(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1	2721.4	Standard polar	33892256
Felbamate,4TMS,isomer #1	C[Si](C)(C)N(C(=O)OCC(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C	2405.7	Semi standard non polar	33892256
Felbamate,4TMS,isomer #1	C[Si](C)(C)N(C(=O)OCC(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C	2440.9	Standard non polar	33892256
Felbamate,4TMS,isomer #1	C[Si](C)(C)N(C(=O)OCC(COC(=O)N([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC=C1)[Si](C)(C)C	2585.6	Standard polar	33892256
Felbamate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	2382.5	Semi standard non polar	33892256
Felbamate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	2320.7	Standard non polar	33892256
Felbamate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(N)=O)C1=CC=CC=C1	3389.5	Standard polar	33892256
Felbamate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(=O)N[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2717.5	Semi standard non polar	33892256
Felbamate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(=O)N[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2585.7	Standard non polar	33892256
Felbamate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(=O)N[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	3023.1	Standard polar	33892256
Felbamate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)OCC(COC(N)=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2669.4	Semi standard non polar	33892256
Felbamate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)OCC(COC(N)=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2618.8	Standard non polar	33892256
Felbamate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(C(=O)OCC(COC(N)=O)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3244.5	Standard polar	33892256
Felbamate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2933.9	Semi standard non polar	33892256
Felbamate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2860.2	Standard non polar	33892256
Felbamate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)OCC(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	2990.2	Standard polar	33892256
Felbamate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)OCC(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3173.7	Semi standard non polar	33892256
Felbamate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)OCC(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	3129.2	Standard non polar	33892256
Felbamate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)OCC(COC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)[Si](C)(C)C(C)(C)C	2924.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Felbamate Metabolism Pathway		Not Available

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 DB00949	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00949	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00949

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3214

KEGG Compound ID

C07501

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Felbamate

METLIN ID

Not Available

PubChem Compound

3331

PDB ID

Not Available

ChEBI ID

4995

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

Leppik IE, Dreifuss FE, Pledger GW, Graves NM, Santilli N, Drury I, Tsay JY, Jacobs MP, Bertram E, Cereghino JJ, et al.: Felbamate for partial seizures: results of a controlled clinical trial. Neurology. 1991 Nov;41(11):1785-9. [PubMed:1944909 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

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 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

3. Cytochrome P450 2E1

General function:: Involved in monooxygenase activity
Specific function:: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:: CYP2E1
Uniprot ID:: P05181
Molecular weight:: 56848.42

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

4. Glutamate [NMDA] receptor subunit epsilon-1

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of subunits
Gene Name:: GRIN2A
Uniprot ID:: Q12879
Molecular weight:: 165281.2

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzyme Details

5. Glutamate [NMDA] receptor subunit epsilon-2

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine
Gene Name:: GRIN2B
Uniprot ID:: Q13224
Molecular weight:: 166365.9

References

Kleckner NW, Glazewski JC, Chen CC, Moscrip TD: Subtype-selective antagonism of N-methyl-D-aspartate receptors by felbamate: insights into the mechanism of action. J Pharmacol Exp Ther. 1999 May;289(2):886-94. [PubMed:10215667 ]
Harty TP, Rogawski MA: Felbamate block of recombinant N-methyl-D-aspartate receptors: selectivity for the NR2B subunit. Epilepsy Res. 2000 Mar;39(1):47-55. [PubMed:10690753 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Chang HR, Kuo CC: Molecular determinants of the anticonvulsant felbamate binding site in the N-methyl-D-aspartate receptor. J Med Chem. 2008 Mar 27;51(6):1534-45. doi: 10.1021/jm0706618. Epub 2008 Feb 27. [PubMed:18311896 ]
Luszczki JJ, Danysz W, Czuczwar SJ: Interactions of MRZ 2/576 with felbamate, lamotrigine, oxcarbazepine and topiramate in the mouse maximal electroshock-induced seizure model. Pharmacology. 2008;81(3):259-65. doi: 10.1159/000114870. Epub 2008 Feb 4. [PubMed:18253065 ]

Enzyme Details

6. Glutamate [NMDA] receptor subunit 3A

General function:: Involved in ionotropic glutamate receptor activity
Specific function:: NMDA receptor subtype of glutamate-gated ion channels with reduced single-channel conductance, low calcium permeability and low voltage-dependent sensitivity to magnesium. Mediated by glycine. May play a role in the development of dendritic spines. May play a role in PPP2CB-NMDAR mediated signaling mechanism
Gene Name:: GRIN3A
Uniprot ID:: Q8TCU5
Molecular weight:: 125464.1

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Showing metabocard for Felbamate (HMDB0015084)

MOL for HMDB0015084 (Felbamate)

3D MOL for HMDB0015084 (Felbamate)

3D SDF for HMDB0015084 (Felbamate)

3D-SDF for HMDB0015084 (Felbamate)

PDB for HMDB0015084 (Felbamate)

3D PDB for HMDB0015084 (Felbamate)

SMILES for HMDB0015084 (Felbamate)

INCHI for HMDB0015084 (Felbamate)

Structure for HMDB0015084 (Felbamate)

3D Structure for HMDB0015084 (Felbamate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

References

References

References

References

References

References