UVI3003   Click here for help

GtoPdb Ligand ID: 2816

Synonyms: compound 10e [PMID: 19408900] | UVI 3003
Compound class: Synthetic organic
Comment: UVI 3003 is a retinoid X receptor (RXR) antagonist [2].

UVI3003 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 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 2
Rotatable bonds 8
Topological polar surface area 66.76
Molecular weight 436.26
XLogP 8.57
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 CCCCCOc1cc2c(cc1c1cc(C=CC(=O)O)ccc1O)C(C)(C)CCC2(C)C
Isomeric SMILES CCCCCOc1cc2c(cc1c1cc(/C=C/C(=O)O)ccc1O)C(C)(C)CCC2(C)C
InChI InChI=1S/C28H36O4/c1-6-7-8-15-32-25-18-23-22(27(2,3)13-14-28(23,4)5)17-21(25)20-16-19(9-11-24(20)29)10-12-26(30)31/h9-12,16-18,29H,6-8,13-15H2,1-5H3,(H,30,31)/b12-10+
InChI Key APJSHECCIRQQDV-ZRDIBKRKSA-N
References
1. Pogenberg V, Guichou JF, Vivat-Hannah V, Kammerer S, Pérez E, Germain P, de Lera AR, Gronemeyer H, Royer CA, Bourguet W. (2005)
Characterization of the interaction between retinoic acid receptor/retinoid X receptor (RAR/RXR) heterodimers and transcriptional coactivators through structural and fluorescence anisotropy studies.
J Biol Chem, 280 (2): 1625-33. [PMID:15528208]
2. Pérez Santín E, Germain P, Quillard F, Khanwalkar H, Rodríguez-Barrios F, Gronemeyer H, de Lera AR, Bourguet W. (2009)
Modulating retinoid X receptor with a series of (E)-3-[4-hydroxy-3-(3-alkoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)phenyl]acrylic acids and their 4-alkoxy isomers.
J Med Chem, 52 (10): 3150-8. [PMID:19408900]