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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 17:53:31 UTC

Update Date

2021-09-26 23:13:21 UTC

HMDB ID

HMDB0257171

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Retigabine

Description

Ezogabine, also known as D-23129 or potiga, belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine. Based on a literature review a significant number of articles have been published on Ezogabine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Retigabine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Retigabine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0257171
     RDKit          3D
Retigabine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.0188    2.0200   -3.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5896    1.6809   -2.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5908    1.6022   -1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5247    0.6729   -1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -0.0356   -2.3265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.6547   -0.2825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444   -0.2058   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -1.1566   -1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030   -1.9561   -1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8272   -1.8326    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -2.6392    0.2388 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795   -2.4337    1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5222   -1.1004    1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163   -0.2920    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0268    0.9662    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7315    1.3837    1.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3242    2.5865    1.2554 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8559    0.6012    2.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2418   -0.6303    2.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5297   -0.8866    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885   -0.0889    0.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706    0.8695    1.8854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7216    2.6774   -4.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7551    1.1027   -4.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0766    2.5883   -3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2700    2.5094   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2188    0.7565   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.3416    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730   -1.2716   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -2.6829   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -3.4072   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -2.4580    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178   -3.2338    1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8631   -0.6294   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    1.5870   -0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4041    0.9035    3.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3404   -1.2464    3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459   -0.7471    1.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9351    1.8636    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088    0.5665    2.8596 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 10 20  1  0
 20 21  2  0
 21 22  1  0
 21  7  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  1  0
M  END


  Mrv0541 02231218032D          

 22 23  0  0  0  0            999 V2000
    4.2365   -4.7439    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    3.5063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    2.2688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.0313    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    2.2688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0930    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -3.5063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    3.9188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    4.7439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 19  1  0  0  0  0
  2 20  1  0  0  0  0
  2 21  1  0  0  0  0
  3 20  2  0  0  0  0
  4  7  1  0  0  0  0
  4  8  1  0  0  0  0
  5 10  1  0  0  0  0
  5 20  1  0  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 13  1  0  0  0  0
  9 15  2  0  0  0  0
  9 16  1  0  0  0  0
 10 12  2  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 15 17  1  0  0  0  0
 16 18  2  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0257171

> <DATABASE_NAME>
hmdb

> <SMILES>
CCOC(=O)NC1=C(N)C=C(NCC2=CC=C(F)C=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)

> <INCHI_KEY>
PCOBBVZJEWWZFR-UHFFFAOYSA-N

> <FORMULA>
C16H18FN3O2

> <MOLECULAR_WEIGHT>
303.3314

> <EXACT_MASS>
303.13830504

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.96538786035255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate

> <ALOGPS_LOGP>
3.07

> <JCHEM_LOGP>
2.698082501

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.604796000020645

> <JCHEM_PKA_STRONGEST_BASIC>
3.989724701450345

> <JCHEM_POLAR_SURFACE_AREA>
76.38

> <JCHEM_REFRACTIVITY>
87.0164

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
retigabine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0257171
     RDKit          3D
Retigabine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.0188    2.0200   -3.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5896    1.6809   -2.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5908    1.6022   -1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5247    0.6729   -1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -0.0356   -2.3265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.6547   -0.2825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444   -0.2058   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -1.1566   -1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030   -1.9561   -1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8272   -1.8326    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -2.6392    0.2388 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795   -2.4337    1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5222   -1.1004    1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163   -0.2920    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0268    0.9662    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7315    1.3837    1.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3242    2.5865    1.2554 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8559    0.6012    2.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2418   -0.6303    2.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5297   -0.8866    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885   -0.0889    0.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706    0.8695    1.8854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7216    2.6774   -4.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7551    1.1027   -4.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0766    2.5883   -3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2700    2.5094   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2188    0.7565   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.3416    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730   -1.2716   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -2.6829   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -3.4072   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -2.4580    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178   -3.2338    1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8631   -0.6294   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    1.5870   -0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4041    0.9035    3.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3404   -1.2464    3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459   -0.7471    1.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9351    1.8636    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088    0.5665    2.8596 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 10 20  1  0
 20 21  2  0
 21 22  1  0
 21  7  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       7.908  -8.855   0.000  0.00  0.00           F+0
HETATM    2  O   UNK     0       7.908   6.545   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       9.242   4.235   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.574  -1.925   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0       6.574   4.235   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       3.907   2.695   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       7.908  -2.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.574  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.908  -4.235   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574   2.695   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.241   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.241   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.908   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.908   1.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.242  -5.005   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -5.005   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.242  -6.545   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.574  -6.545   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.908  -7.315   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.908   5.005   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.242   7.315   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.242   8.855   0.000  0.00  0.00           C+0
CONECT    1   19                                                            
CONECT    2   20   21                                                       
CONECT    3   20                                                            
CONECT    4    7    8                                                       
CONECT    5   10   20                                                       
CONECT    6   12                                                            
CONECT    7    4    9                                                       
CONECT    8    4   11   13                                                  
CONECT    9    7   15   16                                                  
CONECT   10    5   12   14                                                  
CONECT   11    8   12                                                       
CONECT   12    6   10   11                                                  
CONECT   13    8   14                                                       
CONECT   14   10   13                                                       
CONECT   15    9   17                                                       
CONECT   16    9   18                                                       
CONECT   17   15   19                                                       
CONECT   18   16   19                                                       
CONECT   19    1   17   18                                                  
CONECT   20    2    3    5                                                  
CONECT   21    2   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0257171
HETATM    1  C1  UNL     1      -5.019   2.020  -3.579  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.590   1.681  -2.221  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.591   1.602  -1.224  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.525   0.673  -1.320  1.00  0.00           C  
HETATM    5  O2  UNL     1      -3.556  -0.036  -2.327  1.00  0.00           O  
HETATM    6  N1  UNL     1      -2.564   0.655  -0.283  1.00  0.00           N  
HETATM    7  C4  UNL     1      -1.444  -0.206  -0.224  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.134  -1.157  -1.185  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.003  -1.956  -1.031  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.827  -1.833   0.056  1.00  0.00           C  
HETATM   11  N2  UNL     1       1.981  -2.639   0.239  1.00  0.00           N  
HETATM   12  C8  UNL     1       2.879  -2.434   1.348  1.00  0.00           C  
HETATM   13  C9  UNL     1       3.522  -1.100   1.306  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.416  -0.292   0.187  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.027   0.966   0.160  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.731   1.384   1.261  1.00  0.00           C  
HETATM   17  F1  UNL     1       5.324   2.587   1.255  1.00  0.00           F  
HETATM   18  C13 UNL     1       4.856   0.601   2.393  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.242  -0.630   2.383  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.530  -0.887   1.025  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.589  -0.089   0.883  1.00  0.00           C  
HETATM   22  N3  UNL     1      -0.871   0.869   1.885  1.00  0.00           N  
HETATM   23  H1  UNL     1      -5.722   2.677  -4.160  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.755   1.103  -4.163  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.077   2.588  -3.475  1.00  0.00           H  
HETATM   26  H4  UNL     1      -6.270   2.509  -1.944  1.00  0.00           H  
HETATM   27  H5  UNL     1      -6.219   0.756  -2.253  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.676   1.342   0.536  1.00  0.00           H  
HETATM   29  H7  UNL     1      -1.773  -1.272  -2.050  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.215  -2.683  -1.786  1.00  0.00           H  
HETATM   31  H9  UNL     1       2.201  -3.407  -0.440  1.00  0.00           H  
HETATM   32  H10 UNL     1       2.261  -2.458   2.292  1.00  0.00           H  
HETATM   33  H11 UNL     1       3.618  -3.234   1.465  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.863  -0.629  -0.669  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.935   1.587  -0.722  1.00  0.00           H  
HETATM   36  H14 UNL     1       5.404   0.904   3.274  1.00  0.00           H  
HETATM   37  H15 UNL     1       4.340  -1.246   3.275  1.00  0.00           H  
HETATM   38  H16 UNL     1       1.146  -0.747   1.904  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.935   1.864   1.629  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.009   0.566   2.860  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4
CONECT    4    5    5    6
CONECT    6    7   28
CONECT    7    8    8   21
CONECT    8    9   29
CONECT    9   10   10   30
CONECT   10   11   20
CONECT   11   12   31
CONECT   12   13   32   33
CONECT   13   14   14   19
CONECT   14   15   34
CONECT   15   16   16   35
CONECT   16   17   18
CONECT   18   19   19   36
CONECT   19   37
CONECT   20   21   21   38
CONECT   21   22
CONECT   22   39   40
END

HMDB0257171
     RDKit          3D
Retigabine
 40 41  0  0  0  0  0  0  0  0999 V2000
   -5.0188    2.0200   -3.5785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5896    1.6809   -2.2209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5908    1.6022   -1.2241 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5247    0.6729   -1.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560   -0.0356   -2.3265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5644    0.6547   -0.2825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4444   -0.2058   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1336   -1.1566   -1.1847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0030   -1.9561   -1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8272   -1.8326    0.0565 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9813   -2.6392    0.2388 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8795   -2.4337    1.3484 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5222   -1.1004    1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4163   -0.2920    0.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0268    0.9662    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7315    1.3837    1.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3242    2.5865    1.2554 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.8559    0.6012    2.3925 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2418   -0.6303    2.3825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5297   -0.8866    1.0253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885   -0.0889    0.8828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8706    0.8695    1.8854 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7216    2.6774   -4.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7551    1.1027   -4.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0766    2.5883   -3.4753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2700    2.5094   -1.9436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2188    0.7565   -2.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    1.3416    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7730   -1.2716   -2.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2155   -2.6829   -1.7864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2009   -3.4072   -0.4404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2607   -2.4580    2.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6178   -3.2338    1.4647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8631   -0.6294   -0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    1.5870   -0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4041    0.9035    3.2738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3404   -1.2464    3.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1459   -0.7471    1.9041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9351    1.8636    1.6291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0088    0.5665    2.8596 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
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 10 20  1  0
 20 21  2  0
 21 22  1  0
 21  7  1  0
 19 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 22 39  1  0
 22 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
D-23129	ChEBI
Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilate	ChEBI
Ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamate	ChEBI
N-(2-Amino-4-(4-fluorobenzylamino)-phenyl) carbamic acid ethyl ester	ChEBI
N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamic acid ethyl ester	ChEBI
Potiga	ChEBI
Retigabine	ChEBI
Ethyl 2-amino-4-((p-fluorobenzyl)amino)carbanilic acid	Generator
Ethyl {2-amino-4-[(4-fluorobenzyl)amino]phenyl}carbamic acid	Generator
N-(2-Amino-4-(4-fluorobenzylamino)-phenyl) carbamate ethyl ester	Generator
N-(2-Amino-4-(4-fluorobenzylamino)phenyl)carbamate ethyl ester	Generator
Ethyl N-(2-amino-4-(4-fluorobenzylamino)phenyl)carbamate hydrochloride	MeSH
Ezogabine	MeSH

Chemical Formula

C₁₆H₁₈FN₃O₂

Average Molecular Weight

303.3314

Monoisotopic Molecular Weight

303.13830504

IUPAC Name

ethyl N-(2-amino-4-{[(4-fluorophenyl)methyl]amino}phenyl)carbamate

Traditional Name

retigabine

CAS Registry Number

Not Available

SMILES

CCOC(=O)NC1=C(N)C=C(NCC2=CC=C(F)C=C2)C=C1

InChI Identifier

InChI=1S/C16H18FN3O2/c1-2-22-16(21)20-15-8-7-13(9-14(15)18)19-10-11-3-5-12(17)6-4-11/h3-9,19H,2,10,18H2,1H3,(H,20,21)

InChI Key

PCOBBVZJEWWZFR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylbenzamines. These are aromatic compounds consisting of a benzyl group that is N-linked to a benzamine.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylmethylamines

Direct Parent

Phenylbenzamines

Alternative Parents

Substituents

Phenylbenzamine
Benzylamine
Aniline or substituted anilines
Phenylalkylamine
Fluorobenzene
Halobenzene
Secondary aliphatic/aromatic amine
Aralkylamine
Aryl fluoride
Aryl halide
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Secondary amine
Carboximidic acid derivative
Hydrocarbon derivative
Organonitrogen compound
Organofluoride
Organohalogen compound
Amine
Organooxygen compound
Organic nitrogen compound
Primary amine
Organic oxygen compound
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:68584 )
carbamate ester (CHEBI:68584 )
substituted aniline (CHEBI:68584 )
secondary amino compound (CHEBI:68584 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

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
logP	3.07	ALOGPS
logP	2.7	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.6	ChemAxon
pKa (Strongest Basic)	3.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	76.38 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	87.02 m³·mol⁻¹	ChemAxon
Polarizability	31.97 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
DeepCCS	[M+H]+	177.759	30932474
DeepCCS	[M-H]-	175.401	30932474
DeepCCS	[M-2H]-	208.287	30932474
DeepCCS	[M+Na]+	183.852	30932474
AllCCS	[M+H]+	171.4	32859911
AllCCS	[M+H-H2O]+	168.2	32859911
AllCCS	[M+NH4]+	174.4	32859911
AllCCS	[M+Na]+	175.3	32859911
AllCCS	[M-H]-	174.4	32859911
AllCCS	[M+Na-2H]-	174.2	32859911
AllCCS	[M+HCOO]-	174.1	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.	4.85 minutes	32390414
Predicted by Siyang on May 30, 2022	12.8344 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.75 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1741.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	285.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	132.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	411.4 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	534.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	85.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1064.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	337.9 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	1204.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	347.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	283.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	288.8 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	23.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Retigabine	CCOC(=O)NC1=C(N)C=C(NCC2=CC=C(F)C=C2)C=C1	4030.3	Standard polar	33892256
Retigabine	CCOC(=O)NC1=C(N)C=C(NCC2=CC=C(F)C=C2)C=C1	2817.6	Standard non polar	33892256
Retigabine	CCOC(=O)NC1=C(N)C=C(NCC2=CC=C(F)C=C2)C=C1	2719.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Retigabine,1TMS,isomer #1	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C	2841.6	Semi standard non polar	33892256
Retigabine,1TMS,isomer #1	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C	2655.9	Standard non polar	33892256
Retigabine,1TMS,isomer #1	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C	3458.6	Standard polar	33892256
Retigabine,1TMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N)[Si](C)(C)C	2713.5	Semi standard non polar	33892256
Retigabine,1TMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N)[Si](C)(C)C	2491.5	Standard non polar	33892256
Retigabine,1TMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N)[Si](C)(C)C	3449.2	Standard polar	33892256
Retigabine,1TMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N	2705.3	Semi standard non polar	33892256
Retigabine,1TMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N	2503.6	Standard non polar	33892256
Retigabine,1TMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N	3749.4	Standard polar	33892256
Retigabine,2TMS,isomer #1	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C)[Si](C)(C)C	2844.5	Semi standard non polar	33892256
Retigabine,2TMS,isomer #1	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C)[Si](C)(C)C	2586.2	Standard non polar	33892256
Retigabine,2TMS,isomer #1	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C)[Si](C)(C)C	3081.6	Standard polar	33892256
Retigabine,2TMS,isomer #2	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N[Si](C)(C)C	2813.9	Semi standard non polar	33892256
Retigabine,2TMS,isomer #2	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N[Si](C)(C)C	2575.0	Standard non polar	33892256
Retigabine,2TMS,isomer #2	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N[Si](C)(C)C	3233.1	Standard polar	33892256
Retigabine,2TMS,isomer #3	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C	2850.0	Semi standard non polar	33892256
Retigabine,2TMS,isomer #3	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C	2698.3	Standard non polar	33892256
Retigabine,2TMS,isomer #3	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C	3240.3	Standard polar	33892256
Retigabine,2TMS,isomer #4	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N)[Si](C)(C)C	2603.6	Semi standard non polar	33892256
Retigabine,2TMS,isomer #4	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N)[Si](C)(C)C	2507.2	Standard non polar	33892256
Retigabine,2TMS,isomer #4	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N)[Si](C)(C)C	3254.4	Standard polar	33892256
Retigabine,3TMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N[Si](C)(C)C)[Si](C)(C)C	2783.4	Semi standard non polar	33892256
Retigabine,3TMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N[Si](C)(C)C)[Si](C)(C)C	2498.1	Standard non polar	33892256
Retigabine,3TMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N[Si](C)(C)C)[Si](C)(C)C	2907.7	Standard polar	33892256
Retigabine,3TMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2806.2	Semi standard non polar	33892256
Retigabine,3TMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2558.6	Standard non polar	33892256
Retigabine,3TMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2916.5	Standard polar	33892256
Retigabine,3TMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C	2800.9	Semi standard non polar	33892256
Retigabine,3TMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C	2556.9	Standard non polar	33892256
Retigabine,3TMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C	3037.9	Standard polar	33892256
Retigabine,4TMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2735.4	Semi standard non polar	33892256
Retigabine,4TMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2457.7	Standard non polar	33892256
Retigabine,4TMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C)C=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2755.0	Standard polar	33892256
Retigabine,1TBDMS,isomer #1	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C(C)(C)C	3071.1	Semi standard non polar	33892256
Retigabine,1TBDMS,isomer #1	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C(C)(C)C	2871.1	Standard non polar	33892256
Retigabine,1TBDMS,isomer #1	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C(C)(C)C	3535.1	Standard polar	33892256
Retigabine,1TBDMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N)[Si](C)(C)C(C)(C)C	2983.9	Semi standard non polar	33892256
Retigabine,1TBDMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N)[Si](C)(C)C(C)(C)C	2725.6	Standard non polar	33892256
Retigabine,1TBDMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N)[Si](C)(C)C(C)(C)C	3514.0	Standard polar	33892256
Retigabine,1TBDMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N	2952.2	Semi standard non polar	33892256
Retigabine,1TBDMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N	2676.0	Standard non polar	33892256
Retigabine,1TBDMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N	3819.1	Standard polar	33892256
Retigabine,2TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3281.2	Semi standard non polar	33892256
Retigabine,2TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2995.9	Standard non polar	33892256
Retigabine,2TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3290.0	Standard polar	33892256
Retigabine,2TBDMS,isomer #2	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C	3242.7	Semi standard non polar	33892256
Retigabine,2TBDMS,isomer #2	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C	2918.0	Standard non polar	33892256
Retigabine,2TBDMS,isomer #2	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C	3421.1	Standard polar	33892256
Retigabine,2TBDMS,isomer #3	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3310.8	Semi standard non polar	33892256
Retigabine,2TBDMS,isomer #3	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3100.7	Standard non polar	33892256
Retigabine,2TBDMS,isomer #3	CCOC(=O)NC1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3386.9	Standard polar	33892256
Retigabine,2TBDMS,isomer #4	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N)[Si](C)(C)C(C)(C)C	3089.1	Semi standard non polar	33892256
Retigabine,2TBDMS,isomer #4	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N)[Si](C)(C)C(C)(C)C	2874.5	Standard non polar	33892256
Retigabine,2TBDMS,isomer #4	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N)[Si](C)(C)C(C)(C)C	3425.8	Standard polar	33892256
Retigabine,3TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3370.9	Semi standard non polar	33892256
Retigabine,3TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3033.6	Standard non polar	33892256
Retigabine,3TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3216.7	Standard polar	33892256
Retigabine,3TBDMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3456.0	Semi standard non polar	33892256
Retigabine,3TBDMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3201.0	Standard non polar	33892256
Retigabine,3TBDMS,isomer #2	CCOC(=O)N(C1=CC=C(NCC2=CC=C(F)C=C2)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3196.9	Standard polar	33892256
Retigabine,3TBDMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3431.1	Semi standard non polar	33892256
Retigabine,3TBDMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3109.9	Standard non polar	33892256
Retigabine,3TBDMS,isomer #3	CCOC(=O)NC1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3286.4	Standard polar	33892256
Retigabine,4TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3544.2	Semi standard non polar	33892256
Retigabine,4TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3206.4	Standard non polar	33892256
Retigabine,4TBDMS,isomer #1	CCOC(=O)N(C1=CC=C(N(CC2=CC=C(F)C=C2)[Si](C)(C)C(C)(C)C)C=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3132.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Retigabine GC-MS (Non-derivatized) - 70eV, Positive	splash10-057i-4290000000-4b1ff6364c79c0c8b1d2	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Retigabine 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 - Retigabine 10V, Positive-QTOF	splash10-0udr-1093000000-5bb03bf644c85ab30a96	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retigabine 20V, Positive-QTOF	splash10-001i-1190000000-5c8472cf981ca8af2b89	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retigabine 40V, Positive-QTOF	splash10-0gb9-3690000000-26b34859fbe1d2f081d9	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retigabine 10V, Negative-QTOF	splash10-0a4i-2091000000-6dd4d2f8ee3d7e91010b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retigabine 20V, Negative-QTOF	splash10-0a4i-3090000000-d23d9c2d1e1ac8cc16b0	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Retigabine 40V, Negative-QTOF	splash10-00dm-9440000000-061846359c5f729a9d85	2017-07-26	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04953

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

108740

KEGG Compound ID

C13826

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Ezogabine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

68584

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

Enzyme Details

1. Potassium voltage-gated channel subfamily KQT member 2

General function:: Involved in potassium channel activity
Specific function:: Probably important in the regulation of neuronal excitability. Associates with KCNQ3 to form a potassium channel with essentially identical properties to the channel underlying the native M-current, a slowly activating and deactivating potassium conductance which plays a critical role in determining the subthreshold electrical excitability of neurons as well as the responsiveness to synaptic inputs. KCNQ2/KCNQ3 current is blocked by linopirdine and XE991, and activated by the anticonvulsant retigabine. Muscarinic agonist oxotremorine-M strongly suppress KCNQ2/KCNQ3 current in cells in which cloned KCNQ2/KCNQ3 channels were coexpressed with M1 muscarinic receptors
Gene Name:: KCNQ2
Uniprot ID:: O43526
Molecular weight:: 95846.6

Enzyme Details

2. Potassium voltage-gated channel subfamily KQT member 5

General function:: Involved in ion channel activity
Specific function:: Probably important in the regulation of neuronal excitability. Associates with KCNQ3 to form a potassium channel which contributes to M-type current, a slowly activating and deactivating potassium conductance which plays a critical role in determining the subthreshold electrical excitability of neurons. May contribute, with other potassium channels, to the molecular diversity of an heterogeneous population of M-channels, varying in kinetic and pharmacological properties, which underlie this physiologically important current. Insensitive to tetraethylammonium, but inhibited by barium, linopirdine and XE991. Activated by niflumic acid and the anticonvulsant retigabine. Muscarine suppresses KCNQ5 current in Xenopus oocytes in which cloned KCNQ5 channels were coexpressed with M(1) muscarinic receptors
Gene Name:: KCNQ5
Uniprot ID:: Q9NR82
Molecular weight:: 102178.0

Showing metabocard for Retigabine (HMDB0257171)

MOL for HMDB0257171 (Retigabine)

3D MOL for HMDB0257171 (Retigabine)

3D SDF for HMDB0257171 (Retigabine)

3D-SDF for HMDB0257171 (Retigabine)

PDB for HMDB0257171 (Retigabine)

3D PDB for HMDB0257171 (Retigabine)

SMILES for HMDB0257171 (Retigabine)

INCHI for HMDB0257171 (Retigabine)

Structure for HMDB0257171 (Retigabine)

3D Structure for HMDB0257171 (Retigabine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes