General Information of the Compound
Compound ID
CP0221365
Compound Name
(R)-1-(4,4-bis(3-methylthiophen-2-yl)but-3-enyl)piperidine-3-carboxylic acid hydrochloride
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Synonyms
Gabitril
(-)-(R)-1-(4,4-Bis(3-methyl-2-thienyl)-3-butenyl)nipecotic acid
(3R)-1-[4,4-bis(3-methyl-2-thienyl)but-3-en-1-yl]piperidine-3-carboxylic acid
(3R)-1-[4,4-bis(3-methylthiophen-2-yl)but-3-enyl]piperidine-3-carboxylic acid
(R)-1-(4,4-Bis(3-methylthiophen-2-yl)but-3-en-1-yl)piperidine-3-carboxylic acid
(R)-Tiagabine
115103-54-3
A-70569-1
ABBOTT-70569-1
ABT-569
Abbott-70569
CHEBI:9586
CHEMBL1027
Gabatril
Gabitril
Gabitril (TN)
N-(4,4-di(3-methylthien-2-yl)but-3-enyl)nipecotic acid
NO 329
NO-328
NO-329
Tiagabina
Tiagabina [INN-Spanish]
Tiagabina [INN-Spanish];Tiagabine (INN)
Tiagabine
Tiagabine (INN)
Tiagabine [INN:BAN]
Tiagabine [INN]
Tiagabinum
Tiagabinum [INN-Latin]
UNII-Z80I64HMNP
Z80I64HMNP
[3H]tiagabine
tiagabine
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Structure
Formula
C20H25NO2S2
Molecular Weight
375.559
Canonical SMILES
Cc1ccsc1C(=CCCN1CCC[C@H](C1)C(O)=O)c1sccc1C
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InChI
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
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InChIKey
PBJUNZJWGZTSKL-MRXNPFEDSA-N
CAS
115103-54-3
Physicochemical Property
logP
5.04484
Rotatable Bonds
6
Heavy Atom Count
25
Polar Areas
40.54
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Complexity
25

"RO5" indicates the cutoff set by lipinski's rule of five:

(1) Molecular weight less than 500 Dalton;

(2) xlogp less than 5;

(3) No more than 5 hbonddonor (Hydrogen Bond Donor Count);

(4) No more than 10 hbondacc (Hydrogen Bond Acceptor Count);

(5) No more than 10 rotbonds (Rotatable Bond Count).

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PubChem ID
CID: 60648
SID: 14804309
ChEMBL ID
CHEMBL1027
DrugBank ID
DB00906
Map of Molecular Bioactivity Related to the Compound
Map of Molecular Bioactivity Related to the Compound

Compound
Cell Line
Protein

Bioactivity Value:

<= 0.1 μM
> 0.1 μM and <= 10 μM
> 10 μM
Imprecise Activity
Table of Molecular Bioactivities Related to the Compound
Protein ID: PT03285, Sodium- and chloride-dependent GABA transporter 1
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000006 HEK293
 Cell Line Info 
Homo sapiens (Human)  6
1
IC50 = 37.15 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
IC50 = 131.83 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
Ki = 27.54 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
4
Ki = 37.15 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
5
Ki = 38.9 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
6
Ki = 54.95 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000335 D8
 Cell Line Info 
Mus musculus (Mouse)  1
1
IC50 = 191 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 131.83 nM
Protein ID: PT02528, Sodium- and chloride-dependent GABA transporter 1
 Protein Info 
Cell-based Assay
Cell Line ID Cell Line Name Cell Line Organism
CL000880 COS
 Cell Line Info 
Chlorocebus aethiops (Green monkey)  5
1
IC50 = 154.88 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
Kd = 40.5 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
Kd = 146.8 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
4
Km = 19700 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
5
Km = 29400 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
CL000006 HEK293
 Cell Line Info 
Homo sapiens (Human)  3
1
IC50 = 380.19 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
2
Ki = 16.98 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
3
Ki = 47.86 nM
 Bioactivity Info 
   TI
   LI
   LO
   TS
Biochemical Assays
1 IC50 = 70 nM
2 IC50 = 280 nM
Clinical Information about the Compound
Drug 1 ( Tiagabine )
Drug Name Tiagabine
Company Cephalon
Indication
Epilepsy
Approved
Anxiety disorder
Phase 2
Target(s)
GABA transporter GAT-1 (SLC6A1)
 Target Info 
Inhibitor