bexarotene   Click here for help

GtoPdb Ligand ID: 2807

Synonyms: LGD1069 | Targretin® | Targrexin®
Approved drug PDB Ligand
bexarotene is an approved drug (FDA (1999), EMA (2001))
Compound class: Synthetic organic
Comment: Bexarotene is a retinoid that selectively activates retinoid X receptors (RXRs), and is used for its antineoplastic action.
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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

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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 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 37.3
Molecular weight 348.21
XLogP 8.16
No. Lipinski's rules broken 1
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 Cc1cc2c(cc1C(=C)c1ccc(cc1)C(=O)O)C(C)(C)CCC2(C)C
Isomeric SMILES Cc1cc2c(cc1C(=C)c1ccc(cc1)C(=O)O)C(C)(C)CCC2(C)C
InChI InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)
InChI Key NAVMQTYZDKMPEU-UHFFFAOYSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1999), EMA (2001))
IUPAC Name Click here for help
4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid
International Nonproprietary Names Click here for help
INN number INN
7782 bexarotene
Synonyms Click here for help
LGD1069 | Targretin® | Targrexin®
Database Links Click here for help
BindingDB Ligand 50032675
CAS Registry No. 153559-49-0 (source: Scifinder)
ChEBI CHEBI:50859
ChEMBL Ligand CHEMBL1023
DrugBank Ligand DB00307
DrugCentral Ligand 361
GtoPdb PubChem SID 135650520
PubChem CID 82146
RCSB PDB Ligand 9RA
Search Google for chemical match using the InChIKey NAVMQTYZDKMPEU-UHFFFAOYSA-N
Search Google for chemicals with the same backbone NAVMQTYZDKMPEU
Search PubMed clinical trials bexarotene
Search PubMed titles bexarotene
Search PubMed titles/abstracts bexarotene
SynPHARM 83093 (in complex with Peroxisome proliferator-activated receptor-γ)
6486 (in complex with Retinoid X receptor-α)
UniChem Compound Search for chemical match using the InChIKey NAVMQTYZDKMPEU-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey NAVMQTYZDKMPEU-UHFFFAOYSA-N
Wikipedia Bexarotene

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Tocris
Bexarotene (links to external site)
Cat. No. 5819