S18986   Click here for help

GtoPdb Ligand ID: 4304

Synonyms: S 18986 | S-18986
Compound class: Synthetic organic
Comment: S18968 is a positive allosteric modulator of AMPA-type glutamate receptors (an AMPA potentiator), with potential cognition-enhancing properties [1-2]. S18986 corresponds to the S enantiomer.

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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 4
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 57.79
Molecular weight 224.06
XLogP 1.67
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 O=S1(=O)NC2CCCN2c2c1cccc2
Isomeric SMILES O=S1(=O)N[C@H]2CCCN2c2c1cccc2
InChI InChI=1S/C10H12N2O2S/c13-15(14)9-5-2-1-4-8(9)12-7-3-6-10(12)11-15/h1-2,4-5,10-11H,3,6-7H2/t10-/m1/s1
InChI Key MNTIJYGEITVWHU-SNVBAGLBSA-N
Bioactivity Comments
S18986 significantly potentiates AMPA-induced inward currents in a concentration-dependent manner, with an EC50 of 25μM in two-electrode voltage-clamp experiments using Xenopus laevis oocytes injected with rat cortex poly(A+) mRNA [1]. Allostery is indicated by the finding that potentiation is not observed when S18986 is applied in the absence of agonist. S18986 does not interact with the kainate or NMDA glutamate receptors, or with a range of receptors, ion channels or enzymes.
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
GluA1 Hs Allosteric modulator Positive - - -
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GluA2 Hs Allosteric modulator Positive - - -
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GluA3 Hs Allosteric modulator Positive - - -
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GluA4 Hs Allosteric modulator Positive - - -
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Targets where the ligand is described in the comment field
Target Comment
GluA3 Piracetam and aniracetam are examples of pyrrolidinones. Cyclothiazide, S18986, and IDRA-21 are examples of benzothiadiazides. CX516 and CX546 are examples of benzylpiperidines. LY392098, LY404187 and LY503430 are examples of biarylpropylsulfonamides. Also blocked by intracellular polyamines
GluA2 Piracetam and aniracetam are examples of pyrrolidinones. Cyclothiazide, S18986, and IDRA-21 are examples of benzothiadiazides. CX516 and CX546 are examples of benzylpiperidines. LY392098, LY404187 and LY503430 are examples of biarylpropylsulfonamides. Also blocked by intracellular polyamines.
GluA1 Piracetam and aniracetam are examples of pyrrolidinones. Cyclothiazide, S18986, and IDRA-21 are examples of benzothiadiazides. CX516 and CX546 are examples of benzylpiperidines. LY392098, LY404187 and LY503430 are examples of biarylpropylsulfonamides. Also blocked by intracellular polyamines.
GluA4 Piracetam and aniracetam are examples of pyrrolidinones. Cyclothiazide, S18986, and IDRA-21 are examples of benzothiadiazides. CX516 and CX546 are examples of benzylpiperidines. LY392098, LY404187 and LY503430 are examples of biarylpropylsulfonamides. Also blocked by intracellular polyamines