isonipecotic acid   Click here for help

GtoPdb Ligand ID: 4227

PDB Ligand
Compound class: Synthetic organic

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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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 1
Topological polar surface area 49.33
Molecular weight 129.08
XLogP -0.26
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC(=O)C1CCNCC1
Isomeric SMILES OC(=O)C1CCNCC1
InChI InChI=1S/C6H11NO2/c8-6(9)5-1-3-7-4-2-5/h5,7H,1-4H2,(H,8,9)
InChI Key SRJOCJYGOFTFLH-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GABAA receptor α1 subunit Hs Agonist Agonist - - -
⤷ [Binds to: GABA site]
GABAA receptor α2 subunit Hs Agonist Agonist - - -
⤷ [Binds to: GABA site]
GABAA receptor α3 subunit Hs Agonist Agonist - - -
⤷ [Binds to: GABA site]
GABAA receptor α4 subunit Hs Agonist Full agonist - - -
⤷ [Binds to: GABA site] relatively high efficacy, partially selective
GABAA receptor α5 subunit Hs Agonist Agonist - - -
⤷ [Binds to: GABA site]
GABAA receptor α6 subunit Hs Agonist Full agonist - - -
⤷ [Binds to: GABA site] relatively high efficacy, relatively selective
GABAA receptor ρ1 subunit Hs Antagonist Antagonist - - -
⤷ [Binds to: GABA site]
GABAA receptor ρ2 subunit Hs Antagonist Antagonist - - -
⤷ [Binds to: GABA site]
GABAA receptor ρ3 subunit Hs Antagonist Antagonist - - -
⤷ [Binds to: GABA site]