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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:48 UTC

HMDB ID

HMDB0014975

Secondary Accession Numbers

HMDB14975

Metabolite Identification

Common Name

Progabide

Description

Progabide, also known as halogabide or gabrene, belongs to the class of organic compounds known as o-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 2, respectively. Binding to GABAA results in an increased affinity of the GABA receptor for the amino acid, an augmented flux of chloride ions across the terminal membrane, and an increase in the amount of presynaptic inhibition. Progabide is a strong basic compound (based on its pKa). Progabide is an analog and prodrug of gamma-aminobutyric acid. Progabide is a potentially toxic compound. May cause a potentially dangerous rash that may develop into Stevens Johnson syndrome, an extremely rare but potentially fatal skin disease. It has agonistic activity for both the GABAA and GABAB receptors. Activation of the GABAB receptors retards the influx of calcium ions into the terminals, thereby reducing the evoked release of excitatory amino acids and possibly other transmitters.

Structure

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

HMDB0014975
     RDKit          3D
Progabide
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.4511    0.7015    1.8291 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7141    0.2252    0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675    0.0722   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643   -0.0800    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193   -0.5644   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515   -0.9004   -0.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    0.2467   -0.3018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9108    0.1423   -0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    0.4118   -1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698    0.7857   -2.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894    1.0956   -3.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    1.4394   -4.8706 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    1.0703   -3.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5847    0.7467   -2.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600    0.3916   -1.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903    0.0979   -0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5346   -0.3177    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -1.4307    1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -1.7548    2.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6452   -0.9169    3.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3156   -1.2269    5.0049 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814    0.2124    3.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3363    0.5087    2.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9395   -0.0074    2.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4801    1.7306    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9935   -0.7783    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7529    0.8958    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671   -1.5113   -0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603    0.1487   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -1.6987    0.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -1.3254   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170    1.1429   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114    0.8140   -2.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3616    1.3246   -4.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6759    0.7314   -2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440   -2.0994    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4642   -2.6389    2.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993    0.8929    4.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338    1.4223    1.9790 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 15  9  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 23 39  1  0
M  END

837
  Mrv0541 02231215022D          

 23 24  0  0  0  0            999 V2000
    1.6500    0.9034    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -3.2217    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.5717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    1.7284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.3341    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.9659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.7284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.5717    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.7466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.1409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    0.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -3.2217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 23  1  0  0  0  0
  2 18  1  0  0  0  0
  3 14  2  0  0  0  0
  4 17  2  0  0  0  0
  5  7  1  0  0  0  0
  5  9  1  0  0  0  0
  6 17  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  2  0  0  0  0
  9 12  1  0  0  0  0
 10 17  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 12 16  1  0  0  0  0
 13 18  2  0  0  0  0
 14 19  1  0  0  0  0
 15 20  1  0  0  0  0
 16 21  2  0  0  0  0
 18 22  1  0  0  0  0
 19 22  2  0  0  0  0
 20 23  2  0  0  0  0
 21 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014975

> <DATABASE_NAME>
hmdb

> <SMILES>
NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,21H,1-2,9H2,(H2,20,23)/b17-14+

> <INCHI_KEY>
DWEQWXSKOHHBNT-SAPNQHFASA-N

> <FORMULA>
C17H16ClFN2O2

> <MOLECULAR_WEIGHT>
334.773

> <EXACT_MASS>
334.088433678

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.20826964666348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanamide

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
1.7965749693333337

> <ALOGPS_LOGS>
-4.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.315554078461773

> <JCHEM_PKA_STRONGEST_BASIC>
4.014268264490627

> <JCHEM_POLAR_SURFACE_AREA>
72.19

> <JCHEM_REFRACTIVITY>
91.22189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
progabide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014975
     RDKit          3D
Progabide
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.4511    0.7015    1.8291 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7141    0.2252    0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675    0.0722   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643   -0.0800    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193   -0.5644   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515   -0.9004   -0.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    0.2467   -0.3018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9108    0.1423   -0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    0.4118   -1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698    0.7857   -2.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894    1.0956   -3.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    1.4394   -4.8706 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    1.0703   -3.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5847    0.7467   -2.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600    0.3916   -1.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903    0.0979   -0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5346   -0.3177    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -1.4307    1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -1.7548    2.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6452   -0.9169    3.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3156   -1.2269    5.0049 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814    0.2124    3.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3363    0.5087    2.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9395   -0.0074    2.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4801    1.7306    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9935   -0.7783    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7529    0.8958    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671   -1.5113   -0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603    0.1487   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -1.6987    0.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -1.3254   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170    1.1429   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114    0.8140   -2.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3616    1.3246   -4.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6759    0.7314   -2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440   -2.0994    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4642   -2.6389    2.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993    0.8929    4.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338    1.4223    1.9790 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 15  9  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 23 39  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 837                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1 Cl   UNK     0       3.080   1.686   0.000  0.00  0.00          Cl+0
HETATM    2  F   UNK     0      11.082  -6.014   0.000  0.00  0.00           F+0
HETATM    3  O   UNK     0       5.748  -2.934   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      13.750   3.226   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       9.748  -0.624   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0      12.416   5.536   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       9.748   0.916   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.082   1.686   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415  -1.394   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.082   3.226   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.415  -2.934   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.081  -0.624   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.748  -3.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.081  -3.704   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.748  -1.394   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081   0.916   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.416   3.996   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748  -5.244   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.081  -5.244   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.414  -0.624   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.748   1.686   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.415  -6.014   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.414   0.916   0.000  0.00  0.00           C+0
CONECT    1   23                                                            
CONECT    2   18                                                            
CONECT    3   14                                                            
CONECT    4   17                                                            
CONECT    5    7    9                                                       
CONECT    6   17                                                            
CONECT    7    5    8                                                       
CONECT    8    7   10                                                       
CONECT    9    5   11   12                                                  
CONECT   10    8   17                                                       
CONECT   11    9   13   14                                                  
CONECT   12    9   15   16                                                  
CONECT   13   11   18                                                       
CONECT   14    3   11   19                                                  
CONECT   15   12   20                                                       
CONECT   16   12   21                                                       
CONECT   17    4    6   10                                                  
CONECT   18    2   13   22                                                  
CONECT   19   14   22                                                       
CONECT   20   15   23                                                       
CONECT   21   16   23                                                       
CONECT   22   18   19                                                       
CONECT   23    1   20   21                                                  
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0014975
HETATM    1  N1  UNL     1       5.451   0.702   1.829  1.00  0.00           N  
HETATM    2  C1  UNL     1       4.714   0.225   0.706  1.00  0.00           C  
HETATM    3  O1  UNL     1       5.368   0.072  -0.363  1.00  0.00           O  
HETATM    4  C2  UNL     1       3.264  -0.080   0.765  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.819  -0.564  -0.595  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.352  -0.900  -0.627  1.00  0.00           C  
HETATM    7  N2  UNL     1       0.529   0.247  -0.302  1.00  0.00           N  
HETATM    8  C5  UNL     1      -0.911   0.142  -0.275  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.513   0.412  -1.408  1.00  0.00           C  
HETATM   10  C7  UNL     1      -0.770   0.786  -2.625  1.00  0.00           C  
HETATM   11  C8  UNL     1      -1.389   1.096  -3.750  1.00  0.00           C  
HETATM   12  F1  UNL     1      -0.725   1.439  -4.871  1.00  0.00           F  
HETATM   13  C9  UNL     1      -2.857   1.070  -3.801  1.00  0.00           C  
HETATM   14  C10 UNL     1      -3.585   0.747  -2.753  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.960   0.392  -1.470  1.00  0.00           C  
HETATM   16  O2  UNL     1      -3.690   0.098  -0.508  1.00  0.00           O  
HETATM   17  C12 UNL     1      -1.535  -0.318   0.949  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.291  -1.431   1.118  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.860  -1.755   2.340  1.00  0.00           C  
HETATM   20  C15 UNL     1      -2.645  -0.917   3.411  1.00  0.00           C  
HETATM   21 CL1  UNL     1      -3.316  -1.227   5.005  1.00  0.00          CL  
HETATM   22  C16 UNL     1      -1.881   0.212   3.256  1.00  0.00           C  
HETATM   23  C17 UNL     1      -1.336   0.509   2.052  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.939  -0.007   2.428  1.00  0.00           H  
HETATM   25  H2  UNL     1       5.480   1.731   2.017  1.00  0.00           H  
HETATM   26  H3  UNL     1       2.994  -0.778   1.571  1.00  0.00           H  
HETATM   27  H4  UNL     1       2.753   0.896   0.946  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.367  -1.511  -0.828  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.060   0.149  -1.396  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.196  -1.699   0.149  1.00  0.00           H  
HETATM   31  H8  UNL     1       1.029  -1.325  -1.575  1.00  0.00           H  
HETATM   32  H9  UNL     1       1.017   1.143  -0.090  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.311   0.814  -2.620  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.362   1.325  -4.726  1.00  0.00           H  
HETATM   35  H12 UNL     1      -4.676   0.731  -2.802  1.00  0.00           H  
HETATM   36  H13 UNL     1      -2.444  -2.099   0.281  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.464  -2.639   2.481  1.00  0.00           H  
HETATM   38  H15 UNL     1      -1.699   0.893   4.102  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.734   1.422   1.979  1.00  0.00           H  
CONECT    1    2   24   25
CONECT    2    3    3    4
CONECT    4    5   26   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8   32
CONECT    8    9    9   17
CONECT    9   10   15
CONECT   10   11   11   33
CONECT   11   12   13
CONECT   13   14   14   34
CONECT   14   15   35
CONECT   15   16   16
CONECT   17   18   18   23
CONECT   18   19   36
CONECT   19   20   20   37
CONECT   20   21   22
CONECT   22   23   23   38
CONECT   23   39
END

HMDB0014975
     RDKit          3D
Progabide
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.4511    0.7015    1.8291 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7141    0.2252    0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3675    0.0722   -0.3633 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2643   -0.0800    0.7649 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193   -0.5644   -0.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3515   -0.9004   -0.6268 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    0.2467   -0.3018 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9108    0.1423   -0.2751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5126    0.4118   -1.4078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7698    0.7857   -2.6249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3894    1.0956   -3.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7251    1.4394   -4.8706 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573    1.0703   -3.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5847    0.7467   -2.7534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9600    0.3916   -1.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6903    0.0979   -0.5081 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5346   -0.3177    0.9488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2913   -1.4307    1.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8600   -1.7548    2.3399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6452   -0.9169    3.4108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3156   -1.2269    5.0049 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8814    0.2124    3.2556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3363    0.5087    2.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9395   -0.0074    2.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4801    1.7306    2.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9935   -0.7783    1.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7529    0.8958    0.9464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3671   -1.5113   -0.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0603    0.1487   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1961   -1.6987    0.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0289   -1.3254   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0170    1.1429   -0.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3114    0.8140   -2.6202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3616    1.3246   -4.7259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6759    0.7314   -2.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4440   -2.0994    0.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4642   -2.6389    2.4811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6993    0.8929    4.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338    1.4223    1.9790 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  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  8 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 15  9  1  0
 23 17  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
 10 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
 19 37  1  0
 22 38  1  0
 23 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Halogabide	HMDB
Gabrene	HMDB
4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanimidate	Generator
Progabide	MeSH

Chemical Formula

C₁₇H₁₆ClFN₂O₂

Average Molecular Weight

334.773

Monoisotopic Molecular Weight

334.088433678

IUPAC Name

4-{[(4-chlorophenyl)[(1E)-3-fluoro-6-oxocyclohexa-2,4-dien-1-ylidene]methyl]amino}butanamide

Traditional Name

progabide

CAS Registry Number

62666-20-0

SMILES

NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O

InChI Identifier

InChI=1S/C17H16ClFN2O2/c18-12-5-3-11(4-6-12)17(21-9-1-2-16(20)23)14-10-13(19)7-8-15(14)22/h3-8,10,21H,1-2,9H2,(H2,20,23)/b17-14+

InChI Key

DWEQWXSKOHHBNT-SAPNQHFASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-quinomethanes. These are organic compounds containing a benzene ring conjugated to a methylidene group and a ketone at carbon atoms 1 and 2, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

O-quinomethanes

Alternative Parents

Substituents

O-quinomethane
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Vinylogous amide
Carboximidic acid
Carboximidic acid derivative
Secondary aliphatic amine
Enamine
Fluoroalkene
Haloalkene
Secondary amine
Vinyl fluoride
Vinyl halide
Organopnictogen compound
Organic oxide
Amine
Organohalogen compound
Organochloride
Organofluoride
Organonitrogen compound
Hydrocarbon derivative
Organic nitrogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

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

Source

Exogenous

Exogenous (HMDB: HMDB0014975)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	133 - 135 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0044 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0044 g/L	ALOGPS
logP	2.68	ALOGPS
logP	1.8	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	15.32	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	72.19 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	91.22 m³·mol⁻¹	ChemAxon
Polarizability	33.21 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]+	175.218	30932474
DeepCCS	[M-H]-	172.86	30932474
DeepCCS	[M-2H]-	205.746	30932474
DeepCCS	[M+Na]+	181.311	30932474
AllCCS	[M+H]+	175.3	32859911
AllCCS	[M+H-H2O]+	172.1	32859911
AllCCS	[M+NH4]+	178.1	32859911
AllCCS	[M+Na]+	179.0	32859911
AllCCS	[M-H]-	176.3	32859911
AllCCS	[M+Na-2H]-	176.3	32859911
AllCCS	[M+HCOO]-	176.5	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.	6.22 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8196 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.33 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	66.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1707.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	269.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	119.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	377.6 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	385.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	356.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1016.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	412.9 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	1088.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	301.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	350.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	230.7 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	7.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Progabide	NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O	4403.8	Standard polar	33892256
Progabide	NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O	2761.2	Standard non polar	33892256
Progabide	NC(=O)CCCN\C(C1=CC=C(Cl)C=C1)=C1/C=C(F)C=CC1=O	3234.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Progabide,1TMS,isomer #1	C[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3054.5	Semi standard non polar	33892256
Progabide,1TMS,isomer #1	C[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	2901.7	Standard non polar	33892256
Progabide,1TMS,isomer #1	C[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	4107.1	Standard polar	33892256
Progabide,1TMS,isomer #2	C[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3127.1	Semi standard non polar	33892256
Progabide,1TMS,isomer #2	C[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	2687.5	Standard non polar	33892256
Progabide,1TMS,isomer #2	C[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	4171.0	Standard polar	33892256
Progabide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	3137.9	Semi standard non polar	33892256
Progabide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2929.5	Standard non polar	33892256
Progabide,2TMS,isomer #1	C[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	3995.7	Standard polar	33892256
Progabide,2TMS,isomer #2	C[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	3118.8	Semi standard non polar	33892256
Progabide,2TMS,isomer #2	C[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	2895.1	Standard non polar	33892256
Progabide,2TMS,isomer #2	C[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C	3803.0	Standard polar	33892256
Progabide,3TMS,isomer #1	C[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3161.3	Semi standard non polar	33892256
Progabide,3TMS,isomer #1	C[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	2959.8	Standard non polar	33892256
Progabide,3TMS,isomer #1	C[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C)[Si](C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3654.5	Standard polar	33892256
Progabide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3259.3	Semi standard non polar	33892256
Progabide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3106.0	Standard non polar	33892256
Progabide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	4118.6	Standard polar	33892256
Progabide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3368.4	Semi standard non polar	33892256
Progabide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	2890.9	Standard non polar	33892256
Progabide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N(CCCC(N)=O)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	4209.6	Standard polar	33892256
Progabide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3591.7	Semi standard non polar	33892256
Progabide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3317.7	Standard non polar	33892256
Progabide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(C(=O)CCCN/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3987.7	Standard polar	33892256
Progabide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3593.3	Semi standard non polar	33892256
Progabide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3273.2	Standard non polar	33892256
Progabide,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC(=O)CCCN(/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C	3850.8	Standard polar	33892256
Progabide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3843.3	Semi standard non polar	33892256
Progabide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3514.5	Standard non polar	33892256
Progabide,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)/C(=C1\C=C(F)C=CC1=O)C1=CC=C(Cl)C=C1	3749.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Progabide GC-MS (Non-derivatized) - 70eV, Positive	splash10-000x-5091000000-45493775f8e316fed345	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Progabide 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 - Progabide 10V, Positive-QTOF	splash10-00kr-1029000000-fc0da8ed87727a709a1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 20V, Positive-QTOF	splash10-014i-5059000000-63dcad42741a847ae8ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 40V, Positive-QTOF	splash10-000f-9520000000-da113f6ba6c4a6d23a82	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 10V, Negative-QTOF	splash10-001i-0129000000-3de1ea119383317ba355	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 20V, Negative-QTOF	splash10-000y-6289000000-b086ccb10b99604720a8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 40V, Negative-QTOF	splash10-0006-9330000000-2be76f698dbbc120b6b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 10V, Positive-QTOF	splash10-000i-0009000000-513fcdf8c10f3b29cd13	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 20V, Positive-QTOF	splash10-0f80-0094000000-8c5c8a6b47f57d482e91	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 40V, Positive-QTOF	splash10-01q9-0090000000-990d46a622dd2ff2264d	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 10V, Negative-QTOF	splash10-001i-0029000000-8d3aa9ae2fda5750dbf2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 20V, Negative-QTOF	splash10-000t-2196000000-d2a509d2c58ae1850d29	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Progabide 40V, Negative-QTOF	splash10-01qj-3490000000-5a245325ccd99decd7c9	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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 DB00837	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00837	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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4514729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Progabide

METLIN ID

Not Available

PubChem Compound

5361323

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Bartholini G, Scatton B, Zivkovic B, Lloyd KG: GABA receptor agonists and extrapyramidal motor function: therapeutic implications for Parkinson's disease. Adv Neurol. 1987;45:79-83. [PubMed:3030072 ]

Enzymes

Enzyme Details

1. Gamma-aminobutyric acid type B receptor subunit 1

General function:: Involved in G-protein coupled receptor activity
Specific function:: Isoform 1E function may be to regulate the availability of functional GABA-B-R1A/GABA-B-R2 heterodimers by competing for GABA-B-R2 dimerization. This could explain the observation that certain small molecule ligands exhibit differential affinity for central versus peripheral sites
Gene Name:: GABBR1
Uniprot ID:: Q9UBS5
Molecular weight:: 108319.4

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Agmo A, Belzung C: Interactions between dopamine and GABA in the control of ambulatory activity and neophobia in the mouse. Pharmacol Biochem Behav. 1998 Jan;59(1):239-47. [PubMed:9443561 ]
Fadda F, Mosca E, Meloni R, Gessa GL: Suppression by progabide of ethanol withdrawal syndrome in rats. Eur J Pharmacol. 1985 Mar 12;109(3):321-5. [PubMed:2985405 ]

Enzyme Details

2. 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

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 ]
Agmo A, Belzung C: Interactions between dopamine and GABA in the control of ambulatory activity and neophobia in the mouse. Pharmacol Biochem Behav. 1998 Jan;59(1):239-47. [PubMed:9443561 ]
Grech DM, Balster RL: Pentobarbital-like discriminative stimulus effects of direct GABA agonists in rats. Psychopharmacology (Berl). 1993;110(3):295-301. [PubMed:7831422 ]
Fadda F, Mosca E, Meloni R, Gessa GL: Suppression by progabide of ethanol withdrawal syndrome in rats. Eur J Pharmacol. 1985 Mar 12;109(3):321-5. [PubMed:2985405 ]

Showing metabocard for Progabide (HMDB0014975)

MOL for HMDB0014975 (Progabide)

3D MOL for HMDB0014975 (Progabide)

3D SDF for HMDB0014975 (Progabide)

3D-SDF for HMDB0014975 (Progabide)

PDB for HMDB0014975 (Progabide)

3D PDB for HMDB0014975 (Progabide)

SMILES for HMDB0014975 (Progabide)

INCHI for HMDB0014975 (Progabide)

Structure for HMDB0014975 (Progabide)

3D Structure for HMDB0014975 (Progabide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References