gabapentin   Click here for help

GtoPdb Ligand ID: 5483

Synonyms: CI 945 | Go 3450 | GOE 2450 | GOE 3450 | Neurontin®
Approved drug PDB Ligand Immunopharmacology Ligand
gabapentin is an approved drug (FDA (1993))
Compound class: Synthetic organic
Comment: Although gabapentin was desigened to mimic gamma-aminobutyric acid (GABA), it is believed that gabapentinoids act on different brain receptors, such as the α2δ subunit of voltage-gated calcium channels.
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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 171.13
XLogP 1.39
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 NCC1(CCCCC1)CC(=O)O
Isomeric SMILES NCC1(CCCCC1)CC(=O)O
InChI InChI=1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12)
InChI Key UGJMXCAKCUNAIE-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1993))
Prodrug gabapentin enacarbil
IUPAC Name Click here for help
2-[1-(aminomethyl)cyclohexyl]acetic acid
International Nonproprietary Names Click here for help
INN number INN
5094 gabapentin
Synonyms Click here for help
CI 945 | Go 3450 | GOE 2450 | GOE 3450 | Neurontin®
Database Links Click here for help
CAS Registry No. 60142-96-3
ChEMBL Ligand CHEMBL940
DrugBank Ligand DB00996
DrugCentral Ligand 1264
GtoPdb PubChem SID 178102130
PubChem CID 3446
RCSB PDB Ligand GBN
Search Google for chemical match using the InChIKey UGJMXCAKCUNAIE-UHFFFAOYSA-N
Search Google for chemicals with the same backbone UGJMXCAKCUNAIE
Search PubMed clinical trials gabapentin
Search PubMed titles gabapentin
Search PubMed titles/abstracts gabapentin
UniChem Compound Search for chemical match using the InChIKey UGJMXCAKCUNAIE-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey UGJMXCAKCUNAIE-UHFFFAOYSA-N
Wikipedia Gabapentin

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Tocris
Gabapentin (links to external site)
Cat. No. 0806