[3H]Ro154513   Click here for help

GtoPdb Ligand ID: 4365

PDB Ligand  Ligand is labelled  Ligand is radioactive
Compound class: Synthetic organic

[3H]Ro154513 is commercially available from our sponsors

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 7
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 76.27
Molecular weight 326.11
XLogP 2.8
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 CCOC(=O)c1ncn2c1CN(C)C(=O)c1c2ccc(c1)N=[N+]=[N-]
Isomeric SMILES CCOC(=O)c1ncn2c1CN(C)C(=O)c1c2ccc(c1)N=[N+]=[N-]
InChI InChI=1S/C15H14N6O3/c1-3-24-15(23)13-12-7-20(2)14(22)10-6-9(18-19-16)4-5-11(10)21(12)8-17-13/h4-6,8H,3,7H2,1-2H3
InChI Key CFSOJZTUTOQNIA-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 α4 subunit Hs Allosteric modulator Full agonist - - -
⤷ [Binds to: benzodiazepine site]
GABAA receptor α6 subunit Hs Allosteric modulator Full agonist - - -
⤷ [Binds to: benzodiazepine site]
Targets where the ligand is described in the comment field
Target Comment
GABAA receptor α6 subunit Diazepam and flunitrazepam are not active at channels containing this subunit. Zn2+ is an endogenous allosteric regulator and causes potent inhibition of receptors formed from binary combinations of α and β subunits, incorporation of a δ or γ subunit causes a modest, or pronounced, reduction in inhibitory potency, respectively [1]. [3H]Ro154513 selectively labels α6-subunit and α4-subunit-containing receptors in the presence of a saturating concentration of a 'classical' benzodiazepine (e.g. diazepam). Sieghart et al. (2022) provides a review of the pharmacology of α6-containing GABAA receptors.
GABAA receptor α4 subunit Diazepam and flunitrazepam are not active at this subunit. Zn2+ is an endogenous allosteric regulator and causes potent inhibition of receptors formed from binary combinations of α and β subunits, incorporation of a δ or γ subunit causes a modest, or pronounced, reduction in inhibitory potency, respectively [1]. [3H]Ro154513 labels α4βγ2 and α6βγ2 receptors in the presence of a saturating concentration of a 'classical' benzodiazepine (e.g. diazepam).