BF-1   Click here for help

GtoPdb Ligand ID: 8424

Compound class: Synthetic organic
Comment: BF-1 is a selective antagonist of the 5-HT2B receptor, being investigated preclinically as an anti-migraine therapeutic [1]. Because this compound lacks high affinities for other monoamine receptors it should have fewer monoanimergic side effects than reported for previously used and withdrawn 5-HT2B antagonists such as methysergide and pizotifen. BF-1 is the result of structural modification of the chemical scaffold of methixene, a compound with high affinity for 5-HT2A, 2B, 2C, histamine H1, adrenaline α1A and muscarinic M2 receptors [1].
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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
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 1
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 47
Molecular weight 367.16
XLogP 4.29
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 CCOc1ccc2c(c1)Sc1c(C2=C2CCN(CC2)C)c(OC)ccc1
Isomeric SMILES CCOc1ccc2c(c1)Sc1c(C2=C2CCN(CC2)C)c(OC)ccc1
InChI InChI=1S/C22H25NO2S/c1-4-25-16-8-9-17-20(14-16)26-19-7-5-6-18(24-3)22(19)21(17)15-10-12-23(2)13-11-15/h5-9,14H,4,10-13H2,1-3H3
InChI Key ANZVBVKYXOGOQC-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/)
Bioactivity Comments
Binding affinities for BF-1 across the serotinin receptor family and a range of non-serotonin monoaminergic receptors are reported in [1]. We show the affinity for the 2A subtype as the next closest affinity to the 2B receptor in the table below. All other receptors tested had lower affinities for BF-1.
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
5-HT2B receptor Primary target of this compound Hs Antagonist Antagonist 10.1 pKi - 1
⤷ pKi 10.1 [1]
5-HT2A receptor Hs Antagonist Antagonist 8.6 pKi - 1
⤷ pKi 8.6 [1]