GABA   Click here for help

GtoPdb Ligand ID: 1067

Synonyms: γ-amino butyric acid | 4-aminobutyric acid | gamma-aminobutyric acid
PDB Ligand
Compound class: Metabolite or derivative
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 63.32
Molecular weight 103.06
XLogP -0.67
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NCCCC(=O)O
Isomeric SMILES NCCCC(=O)O
InChI InChI=1S/C4H9NO2/c5-3-1-2-4(6)7/h1-3,5H2,(H,6,7)
InChI Key BTCSSZJGUNDROE-UHFFFAOYSA-N
References
1. Anderson CM, Howard A, Walters JR, Ganapathy V, Thwaites DT. (2009)
Taurine uptake across the human intestinal brush-border membrane is via two transporters: H+-coupled PAT1 (SLC36A1) and Na+- and Cl(-)-dependent TauT (SLC6A6).
J Physiol (Lond.), 587 (Pt 4): 731-44. [PMID:19074966]
2. De Saint Jan D, David-Watine B, Korn H, Bregestovski P. (2001)
Activation of human alpha1 and alpha2 homomeric glycine receptors by taurine and GABA.
J Physiol (Lond.), 535 (Pt 3): 741-55. [PMID:11559772]
3. Froestl W, Mickel SJ. (1997)
Chemistry of GABAB modulators.  In  The GABA Receptors
Edited by Enna SJ, Bowery NG (Humana Press) 271-296. [ISBN:0896034585]
4. Hirst WD, Babbs AJ, Green A, Minton JA, Shaw TE, Wise A, Rice SQ, Pangalos MN, Price GW. (2003)
Pharmacological characterisation of a cell line expressing GABA B1b and GABA B2 receptor subunits.
Biochem Pharmacol, 65 (7): 1103-13. [PMID:12663046]
5. Kaupmann K, Huggel K, Heid J, Flor PJ, Bischoff S, Mickel SJ, McMaster G, Angst C, Bittiger H, Froestl W et al.. (1997)
Expression cloning of GABA(B) receptors uncovers similarity to metabotropic glutamate receptors.
Nature, 386 (6622): 239-46. [PMID:9069281]
6. McIntire SL, Reimer RJ, Schuske K, Edwards RH, Jorgensen EM. (1997)
Identification and characterization of the vesicular GABA transporter.
Nature, 389 (6653): 870-6. [PMID:9349821]
7. Schmieden V, Kuhse J, Betz H. (1993)
Mutation of glycine receptor subunit creates beta-alanine receptor responsive to GABA.
Science, 262 (5131): 256-8. [PMID:8211147]
8. Thwaites DT, Anderson CM. (2011)
The SLC36 family of proton-coupled amino acid transporters and their potential role in drug transport.
Br J Pharmacol, 164 (7): 1802-16. [PMID:21501141]
9. Wood MD, Murkitt KL, Rice SQ, Testa T, Punia PK, Stammers M, Jenkins O, Elshourbagy NA, Shabon U, Taylor SJ et al.. (2000)
The human GABA(B1b) and GABA(B2) heterodimeric recombinant receptor shows low sensitivity to phaclofen and saclofen.
Br J Pharmacol, 131 (6): 1050-4. [PMID:11082110]