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K-80003   Click here for help

GtoPdb Ligand ID: 10347

PDB Ligand
Compound class: Synthetic organic
Comment: K-80003 ia a retinoid X receptor-α (RXRα) modulator [1] that can attenuate atherosclerotic plaque progression and destabilization in the ApoE-/- mouse model. Structurally, K-80003 is an analogue of the NSAID sulindac, but it lacks the COX inhibitory activity of the parent molecule [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

K-80003 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 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 37.3
Molecular weight 336.15
XLogP 6.32
No. Lipinski's rules broken 1

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)CC1=C(C)C(=Cc2ccc(cc2)C(C)C)c2c1cc(F)cc2
Isomeric SMILES OC(=O)CC1=C(C)/C(=C/c2ccc(cc2)C(C)C)/c2c1cc(F)cc2
InChI InChI=1S/C22H21FO2/c1-13(2)16-6-4-15(5-7-16)10-19-14(3)20(12-22(24)25)21-11-17(23)8-9-18(19)21/h4-11,13H,12H2,1-3H3,(H,24,25)/b19-10-
InChI Key QCXBVGNDRYQVJO-GRSHGNNSSA-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
2-[(3Z)-6-fluoro-2-methyl-3-[(4-propan-2-ylphenyl)methylidene]inden-1-yl]acetic acid
Database Links Click here for help
CAS Registry No. 1292821-90-9 (source: PubChem)
GtoPdb PubChem SID 381745028
PubChem CID 46224594
RCSB PDB Ligand 7A4
Search Google for chemical match using the InChIKey QCXBVGNDRYQVJO-GRSHGNNSSA-N
Search Google for chemicals with the same backbone QCXBVGNDRYQVJO
UniChem Compound Search for chemical match using the InChIKey QCXBVGNDRYQVJO-GRSHGNNSSA-N
UniChem Connectivity Search for chemical match using the InChIKey QCXBVGNDRYQVJO-GRSHGNNSSA-N

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MedChemExpress
K-80003 (links to external site)
Cat. No. HY-U00458