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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

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:50 UTC

HMDB ID

HMDB0015042

Secondary Accession Numbers

HMDB15042

Metabolite Identification

Common Name

Tiagabine

Description

Tiagabine, also known as gabitril or (R)-tiagabine, belongs to the class of organic compounds known as piperidinecarboxylic acids. Piperidinecarboxylic acids are compounds containing a piperidine ring which bears a carboxylic acid group. Tiagabine is a drug which is used for the treatment of partial seizures. Based on a literature review a significant number of articles have been published on Tiagabine.

Structure

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

HMDB0015042
     RDKit          3D
Tiagabine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.8298    1.0072    1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2489    1.7301    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    2.6227   -0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4277    3.3316   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312    2.7449   -1.5176 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634    1.5948   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    0.6909    0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332    1.1773    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301    0.4862    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664    0.4992   -0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -0.1383   -0.8289 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6848   -1.5482   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442   -2.1616   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914   -1.2196   -0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351    0.1258    0.0179 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4667    1.1469   -0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310    0.8104   -2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3610    2.5196   -0.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980    0.4430    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316   -0.6284    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -1.5031    1.9093 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610   -2.9839    1.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0147   -2.7666    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0598   -1.5686    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0369   -1.3001   -0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6695    0.3743    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    0.4924    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3053    1.8183    2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1072    2.8176   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9040    4.0981   -2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5427    2.2109   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5378   -0.5876    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343    1.0370    1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -0.0115   -1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218    1.5405   -1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0216   -2.0799   -1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2138   -1.7344    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063   -2.9463    0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -2.7797   -1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013   -1.1551   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9851   -1.7036    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5049    0.3213    0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    3.1239   -1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610   -0.0258    1.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    1.5458    0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034   -3.9169    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -3.5935    0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6096   -0.5236   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0616   -1.2094   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -2.2251   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
  7 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  6  2  2  0
 19 11  1  0
 24 20  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  1
 18 43  1  0
 19 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
M  END

906
  Mrv0541 02231215052D          

 25 27  0  0  1  0            999 V2000
    6.0232   -0.3227    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.8899   -2.8656    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    3.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    2.1569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.9194    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    2.1569    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0791    1.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    2.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    2.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.1431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6906   -1.4787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5550   -2.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2427   -0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8099   -3.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8622   -2.2857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7704   -2.6106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8302   -0.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6350   -3.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 16  1  0  0  0  0
  1 24  1  0  0  0  0
  2 17  1  0  0  0  0
  2 25  1  0  0  0  0
  3 13  1  0  0  0  0
  4 13  2  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  6 13  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  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 20  1  0  0  0  0
 18 22  1  0  0  0  0
 19 21  1  0  0  0  0
 19 23  1  0  0  0  0
 20 24  2  0  0  0  0
 21 25  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015042

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(SC=C1)C(=CCCN1CCC[C@H](C1)C(O)=O)C1=C(C)C=CS1

> <INCHI_IDENTIFIER>
InChI=1S/C20H25NO2S2/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23)/t16-/m1/s1

> <INCHI_KEY>
PBJUNZJWGZTSKL-MRXNPFEDSA-N

> <FORMULA>
C20H25NO2S2

> <MOLECULAR_WEIGHT>
375.548

> <EXACT_MASS>
375.132670429

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
41.69658064063397

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid

> <ALOGPS_LOGP>
4.98

> <JCHEM_LOGP>
2.6014484715409854

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.143309589728766

> <JCHEM_PKA_STRONGEST_BASIC>
9.256939516244088

> <JCHEM_POLAR_SURFACE_AREA>
40.54

> <JCHEM_REFRACTIVITY>
115.31710000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tiagabine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015042
     RDKit          3D
Tiagabine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.8298    1.0072    1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2489    1.7301    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    2.6227   -0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4277    3.3316   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312    2.7449   -1.5176 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634    1.5948   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    0.6909    0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332    1.1773    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301    0.4862    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664    0.4992   -0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -0.1383   -0.8289 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6848   -1.5482   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442   -2.1616   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914   -1.2196   -0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351    0.1258    0.0179 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4667    1.1469   -0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310    0.8104   -2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3610    2.5196   -0.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980    0.4430    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316   -0.6284    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -1.5031    1.9093 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610   -2.9839    1.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0147   -2.7666    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0598   -1.5686    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0369   -1.3001   -0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6695    0.3743    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    0.4924    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3053    1.8183    2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1072    2.8176   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9040    4.0981   -2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5427    2.2109   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5378   -0.5876    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343    1.0370    1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -0.0115   -1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218    1.5405   -1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0216   -2.0799   -1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2138   -1.7344    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063   -2.9463    0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -2.7797   -1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013   -1.1551   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9851   -1.7036    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5049    0.3213    0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    3.1239   -1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610   -0.0258    1.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    1.5458    0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034   -3.9169    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -3.5935    0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6096   -0.5236   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0616   -1.2094   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -2.2251   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
  7 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  6  2  2  0
 19 11  1  0
 24 20  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  1
 18 43  1  0
 19 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 906                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      11.243  -0.602   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      10.994  -5.349   0.000  0.00  0.00           S+0
HETATM    3  O   UNK     0       4.414   6.336   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.080   4.026   0.000  0.00  0.00           O+0
HETATM    5  N   UNK     0       7.081   1.716   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       5.748   4.026   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748   2.486   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081   4.796   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.415   4.026   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.415   2.486   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.081   0.176   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -0.594   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.414   4.796   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.415  -2.134   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -2.904   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.082  -2.134   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748  -4.444   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.489  -2.760   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.503  -5.349   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.520  -1.616   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.978  -6.814   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.809  -4.267   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.038  -4.873   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.750  -0.282   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.519  -6.814   0.000  0.00  0.00           C+0
CONECT    1   16   24                                                       
CONECT    2   17   25                                                       
CONECT    3   13                                                            
CONECT    4   13                                                            
CONECT    5    7   10   11                                                  
CONECT    6    7    8   13                                                  
CONECT    7    5    6                                                       
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9                                                       
CONECT   11    5   12                                                       
CONECT   12   11   14                                                       
CONECT   13    3    4    6                                                  
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16    1   15   18                                                  
CONECT   17    2   15   19                                                  
CONECT   18   16   20   22                                                  
CONECT   19   17   21   23                                                  
CONECT   20   18   24                                                       
CONECT   21   19   25                                                       
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24    1   20                                                       
CONECT   25    2   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   54    0
END

COMPND    HMDB0015042
HETATM    1  C1  UNL     1      -4.830   1.007   1.358  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.249   1.730   0.146  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.023   2.623  -0.519  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.428   3.332  -1.524  1.00  0.00           C  
HETATM    5  S1  UNL     1      -2.831   2.745  -1.518  1.00  0.00           S  
HETATM    6  C5  UNL     1      -2.963   1.595  -0.221  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.865   0.691   0.155  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.633   1.177   0.000  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.630   0.486   0.294  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.466   0.499  -0.997  1.00  0.00           C  
HETATM   11  N1  UNL     1       2.727  -0.138  -0.829  1.00  0.00           N  
HETATM   12  C10 UNL     1       2.685  -1.548  -0.627  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.044  -2.162  -0.591  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.191  -1.220  -0.553  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.935   0.126   0.018  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.467   1.147  -0.952  1.00  0.00           C  
HETATM   17  O1  UNL     1       6.031   0.810  -2.029  1.00  0.00           O  
HETATM   18  O2  UNL     1       5.361   2.520  -0.708  1.00  0.00           O  
HETATM   19  C15 UNL     1       3.498   0.443   0.262  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.132  -0.628   0.711  1.00  0.00           C  
HETATM   21  S2  UNL     1      -1.237  -1.503   1.909  1.00  0.00           S  
HETATM   22  C17 UNL     1      -2.061  -2.984   1.866  1.00  0.00           C  
HETATM   23  C18 UNL     1      -3.015  -2.767   0.917  1.00  0.00           C  
HETATM   24  C19 UNL     1      -3.060  -1.569   0.319  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.037  -1.300  -0.828  1.00  0.00           C  
HETATM   26  H1  UNL     1      -5.669   0.374   1.071  1.00  0.00           H  
HETATM   27  H2  UNL     1      -4.078   0.492   1.931  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.305   1.818   2.007  1.00  0.00           H  
HETATM   29  H4  UNL     1      -6.107   2.818  -0.305  1.00  0.00           H  
HETATM   30  H5  UNL     1      -4.904   4.098  -2.168  1.00  0.00           H  
HETATM   31  H6  UNL     1      -0.543   2.211  -0.391  1.00  0.00           H  
HETATM   32  H7  UNL     1       0.538  -0.588   0.531  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.234   1.037   1.039  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.905  -0.012  -1.809  1.00  0.00           H  
HETATM   35  H10 UNL     1       1.622   1.540  -1.356  1.00  0.00           H  
HETATM   36  H11 UNL     1       2.022  -2.080  -1.348  1.00  0.00           H  
HETATM   37  H12 UNL     1       2.214  -1.734   0.377  1.00  0.00           H  
HETATM   38  H13 UNL     1       4.106  -2.946   0.222  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.154  -2.780  -1.531  1.00  0.00           H  
HETATM   40  H15 UNL     1       5.701  -1.155  -1.560  1.00  0.00           H  
HETATM   41  H16 UNL     1       5.985  -1.704   0.094  1.00  0.00           H  
HETATM   42  H17 UNL     1       5.505   0.321   0.968  1.00  0.00           H  
HETATM   43  H18 UNL     1       4.787   3.124  -1.289  1.00  0.00           H  
HETATM   44  H19 UNL     1       3.161  -0.026   1.192  1.00  0.00           H  
HETATM   45  H20 UNL     1       3.336   1.546   0.329  1.00  0.00           H  
HETATM   46  H21 UNL     1      -1.903  -3.917   2.440  1.00  0.00           H  
HETATM   47  H22 UNL     1      -3.727  -3.593   0.672  1.00  0.00           H  
HETATM   48  H23 UNL     1      -3.610  -0.524  -1.444  1.00  0.00           H  
HETATM   49  H24 UNL     1      -5.062  -1.209  -0.490  1.00  0.00           H  
HETATM   50  H25 UNL     1      -4.035  -2.225  -1.486  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    6    6
CONECT    3    4    4   29
CONECT    4    5   30
CONECT    5    6
CONECT    6    7
CONECT    7    8    8   20
CONECT    8    9   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12   19
CONECT   12   13   36   37
CONECT   13   14   38   39
CONECT   14   15   40   41
CONECT   15   16   19   42
CONECT   16   17   17   18
CONECT   18   43
CONECT   19   44   45
CONECT   20   21   24   24
CONECT   21   22
CONECT   22   23   23   46
CONECT   23   24   47
CONECT   24   25
CONECT   25   48   49   50
END

HMDB0015042
     RDKit          3D
Tiagabine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.8298    1.0072    1.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2489    1.7301    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    2.6227   -0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4277    3.3316   -1.5244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8312    2.7449   -1.5176 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634    1.5948   -0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8646    0.6909    0.1551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6332    1.1773    0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6301    0.4862    0.2943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4664    0.4992   -0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7266   -0.1383   -0.8289 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6848   -1.5482   -0.6270 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0442   -2.1616   -0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1914   -1.2196   -0.5528 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9351    0.1258    0.0179 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4667    1.1469   -0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0310    0.8104   -2.0295 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3610    2.5196   -0.7076 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980    0.4430    0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1316   -0.6284    0.7105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -1.5031    1.9093 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0610   -2.9839    1.8659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0147   -2.7666    0.9170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0598   -1.5686    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0369   -1.3001   -0.8276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6695    0.3743    1.0710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0783    0.4924    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3053    1.8183    2.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1072    2.8176   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9040    4.0981   -2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5427    2.2109   -0.3906 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5378   -0.5876    0.5305 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2343    1.0370    1.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9050   -0.0115   -1.8088 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6218    1.5405   -1.3556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0216   -2.0799   -1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2138   -1.7344    0.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063   -2.9463    0.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1537   -2.7797   -1.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7013   -1.1551   -1.5598 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9851   -1.7036    0.0937 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5049    0.3213    0.9675 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7874    3.1239   -1.2886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1610   -0.0258    1.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3362    1.5458    0.3286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034   -3.9169    2.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7267   -3.5935    0.6719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6096   -0.5236   -1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0616   -1.2094   -0.4899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0350   -2.2251   -1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 15 19  1  0
  7 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  6  2  2  0
 19 11  1  0
 24 20  2  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 14 40  1  0
 14 41  1  0
 15 42  1  1
 18 43  1  0
 19 44  1  0
 19 45  1  0
 22 46  1  0
 23 47  1  0
 25 48  1  0
 25 49  1  0
 25 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acid	ChEBI
(-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid	ChEBI
(R)-(-)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotic acid	ChEBI
(R)-Tiagabine	ChEBI
Tiagabina	ChEBI
Tiagabinum	ChEBI
Gabitril	Kegg
(-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotate	Generator
(-)-(R)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotate	Generator
(R)-(-)-1-[4,4-Bis(3-methyl-2-thienyl)-3-butenyl]nipecotate	Generator
Tiagabine, (S)-isomer	HMDB
(R)-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)-3-piperidinecarboxylic acid, hydrochloride	HMDB
N-(4,4-Di(3-methylthien-2-yl)but-3-enyl)nipecotic acid	HMDB
Tiagabine hydrochloride	HMDB

Chemical Formula

C₂₀H₂₅NO₂S₂

Average Molecular Weight

375.548

Monoisotopic Molecular Weight

375.132670429

IUPAC Name

(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-en-1-yl]piperidine-3-carboxylic acid

Traditional Name

tiagabine

CAS Registry Number

115103-54-3

SMILES

CC1=C(SC=C1)C(=CCCN1CCC[C@H](C1)C(O)=O)C1=C(C)C=CS1

InChI Identifier

InChI=1S/C20H25NO2S2/c1-14-7-11-24-18(14)17(19-15(2)8-12-25-19)6-4-10-21-9-3-5-16(13-21)20(22)23/h6-8,11-12,16H,3-5,9-10,13H2,1-2H3,(H,22,23)/t16-/m1/s1

InChI Key

PBJUNZJWGZTSKL-MRXNPFEDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as piperidinecarboxylic acids. Piperidinecarboxylic acids are compounds containing a piperidine ring which bears a carboxylic acid group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Piperidinecarboxylic acids and derivatives

Direct Parent

Piperidinecarboxylic acids

Alternative Parents

Substituents

Piperidinecarboxylic acid
Thiophene
Heteroaromatic compound
Amino acid or derivatives
Tertiary amine
Amino acid
Tertiary aliphatic amine
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

tertiary amino compound (CHEBI:9586 )
thiophenes (CHEBI:9586 )
piperidinemonocarboxylic acid (CHEBI:9586 )
beta-amino acid (CHEBI:9586 )

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: HMDB0015042)

Source

Exogenous

Exogenous (HMDB: HMDB0015042)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.021 g/L	Not Available
LogP	2.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	184.5	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.021 g/L	ALOGPS
logP	4.98	ALOGPS
logP	2.6	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	9.26	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	40.54 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.32 m³·mol⁻¹	ChemAxon
Polarizability	41.7 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	184.784	31661259
DarkChem	[M-H]-	175.455	31661259
DeepCCS	[M+H]+	183.504	30932474
DeepCCS	[M-H]-	181.146	30932474
DeepCCS	[M-2H]-	215.443	30932474
DeepCCS	[M+Na]+	190.607	30932474
AllCCS	[M+H]+	188.1	32859911
AllCCS	[M+H-H2O]+	185.3	32859911
AllCCS	[M+NH4]+	190.7	32859911
AllCCS	[M+Na]+	191.4	32859911
AllCCS	[M-H]-	190.6	32859911
AllCCS	[M+Na-2H]-	190.7	32859911
AllCCS	[M+HCOO]-	190.9	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.	5.6 minutes	32390414
Predicted by Siyang on May 30, 2022	11.8889 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.6 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	59.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1405.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	221.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	183.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	138.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	477.5 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	430.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	270.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1011.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	422.0 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	1399.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	303.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	378.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	347.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	157.1 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	15.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tiagabine	CC1=C(SC=C1)C(=CCCN1CCC[C@H](C1)C(O)=O)C1=C(C)C=CS1	4203.9	Standard polar	33892256
Tiagabine	CC1=C(SC=C1)C(=CCCN1CCC[C@H](C1)C(O)=O)C1=C(C)C=CS1	2897.6	Standard non polar	33892256
Tiagabine	CC1=C(SC=C1)C(=CCCN1CCC[C@H](C1)C(O)=O)C1=C(C)C=CS1	3154.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tiagabine,1TMS,isomer #1	CC1=C(C(=CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C)C2)C2=C(C)C=CS2)SC=C1	3047.1	Semi standard non polar	33892256
Tiagabine,1TBDMS,isomer #1	CC1=C(C(=CCCN2CCC[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C2)C2=C(C)C=CS2)SC=C1	3287.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tiagabine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-9421000000-a3d6cacc1c1eda797cdc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiagabine GC-MS (1 TMS) - 70eV, Positive	splash10-00e9-9141000000-ad3f282e81f21efc67a4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tiagabine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tiagabine , positive-QTOF	splash10-004j-1769000000-3559976e948cc2135c8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tiagabine 35V, Positive-QTOF	splash10-004j-0984000000-a978c5e709fb0da0ceca	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Tiagabine 35V, Negative-QTOF	splash10-004i-0901000000-f4977b5cba740f9bf146	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 10V, Positive-QTOF	splash10-004i-0029000000-c5f87e6c22eea721b905	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 20V, Positive-QTOF	splash10-0a6s-1298000000-59e359809fb473d67bb3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 40V, Positive-QTOF	splash10-0a4j-4190000000-98420f8a2019b820d741	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 10V, Negative-QTOF	splash10-00di-1009000000-bd93b21b33d14728f6cb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 20V, Negative-QTOF	splash10-001i-6119000000-718202039949c898877e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 40V, Negative-QTOF	splash10-0a5a-9011000000-8572588cb43983c9c799	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 10V, Positive-QTOF	splash10-004i-0019000000-85f99d6f70a9fbf994d2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 20V, Positive-QTOF	splash10-0a4j-0049000000-db812ecf5f7fb1975926	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 40V, Positive-QTOF	splash10-0002-9032000000-b4c12faa49251f4425b0	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 10V, Negative-QTOF	splash10-00di-0009000000-75b21c9b910e4d5d90b6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 20V, Negative-QTOF	splash10-00di-0039000000-b8393c7a9d1fdd48a1a2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tiagabine 40V, Negative-QTOF	splash10-00r2-5294000000-26284b1d5f7adf9241ff	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00906	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00906	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

DB00906

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54661

KEGG Compound ID

C07503

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tiagabine

METLIN ID

Not Available

PubChem Compound

60648

PDB ID

Not Available

ChEBI ID

9586

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Cytochrome P450 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. Sodium- and chloride-dependent GABA transporter 1

General function:: Involved in neurotransmitter:sodium symporter activity
Specific function:: Terminates the action of GABA by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:: SLC6A1
Uniprot ID:: P30531
Molecular weight:: 67073.0

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Pollack MH, Roy-Byrne PP, Van Ameringen M, Snyder H, Brown C, Ondrasik J, Rickels K: The selective GABA reuptake inhibitor tiagabine for the treatment of generalized anxiety disorder: results of a placebo-controlled study. J Clin Psychiatry. 2005 Nov;66(11):1401-8. [PubMed:16420077 ]
Sheehan DV, Sheehan KH, Raj BA, Janavs J: An open-label study of tiagabine in panic disorder. Psychopharmacol Bull. 2007;40(3):32-40. [PubMed:18007567 ]
Foster AC, Kemp JA: Glutamate- and GABA-based CNS therapeutics. Curr Opin Pharmacol. 2006 Feb;6(1):7-17. Epub 2005 Dec 22. [PubMed:16377242 ]
Sunol C, Babot Z, Cristofol R, Sonnewald U, Waagepetersen HS, Schousboe A: A possible role of the non-GAT1 GABA transporters in transfer of GABA from GABAergic to glutamatergic neurons in mouse cerebellar neuronal cultures. Neurochem Res. 2010 Sep;35(9):1384-90. doi: 10.1007/s11064-010-0196-1. Epub 2010 May 30. [PubMed:20512624 ]
Henjum S, Hassel B: High-affinity GABA uptake and GABA-metabolizing enzymes in pig forebrain white matter: a quantitative study. Neurochem Int. 2007 Jan;50(2):365-70. Epub 2006 Oct 27. [PubMed:17069932 ]

Showing metabocard for Tiagabine (HMDB0015042)

MOL for HMDB0015042 (Tiagabine)

3D MOL for HMDB0015042 (Tiagabine)

3D SDF for HMDB0015042 (Tiagabine)

3D-SDF for HMDB0015042 (Tiagabine)

PDB for HMDB0015042 (Tiagabine)

3D PDB for HMDB0015042 (Tiagabine)

SMILES for HMDB0015042 (Tiagabine)

INCHI for HMDB0015042 (Tiagabine)

Structure for HMDB0015042 (Tiagabine)

3D Structure for HMDB0015042 (Tiagabine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References