(R)-flurbiprofen   Click here for help

GtoPdb Ligand ID: 7340

Synonyms: MPC-7869
PDB Ligand
Compound class: Synthetic organic
Comment: Tarenflurbil or R-flurbiprofen, is the single enantiomer of the racemate NSAID flurbiprofen. Research and trials for Alzheimer's disease were conducted by Myriad Genetics but the company discontinued development in 2008. This compound is the archetypal γ-secretase modulator (GSM) that blocks γ-secretase cleavage of amyloid-β protein precursor (AβPP) to generate the longer, 42-residue amyloid-β (Aβ42) without changing the production of total Aβ (e.g. CHF5074) [2].
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 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 37.3
Molecular weight 244.09
XLogP 3.76
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)C(c1ccc(c(c1)F)c1ccccc1)C
Isomeric SMILES OC(=O)[C@@H](c1ccc(c(c1)F)c1ccccc1)C
InChI InChI=1S/C15H13FO2/c1-10(15(17)18)12-7-8-13(14(16)9-12)11-5-3-2-4-6-11/h2-10H,1H3,(H,17,18)/t10-/m1/s1
InChI Key SYTBZMRGLBWNTM-SNVBAGLBSA-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/)
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(2R)-2-(3-fluoro-4-phenylphenyl)propanoic acid
International Nonproprietary Names Click here for help
INN number INN
3220 flurbiprofen
8417 tarenflurbil
Synonyms Click here for help
MPC-7869
Database Links Click here for help
CAS Registry No. 51543-40-9 (source: Scifinder)
ChEBI CHEBI:38666
ChEMBL Ligand CHEMBL190083
DrugBank Ligand DB05289
GtoPdb PubChem SID 178103912
PubChem CID 92337
RCSB PDB Ligand FLR
Search Google for chemical match using the InChIKey SYTBZMRGLBWNTM-SNVBAGLBSA-N
Search Google for chemicals with the same backbone SYTBZMRGLBWNTM
Search PubMed clinical trials tarenflurbil
Search PubMed titles tarenflurbil
Search PubMed titles/abstracts tarenflurbil
UniChem Compound Search for chemical match using the InChIKey SYTBZMRGLBWNTM-SNVBAGLBSA-N
UniChem Connectivity Search for chemical match using the InChIKey SYTBZMRGLBWNTM-SNVBAGLBSA-N
Wikipedia Tarenflurbil