alitretinoin   Click here for help

GtoPdb Ligand ID: 2645

Synonyms: 9-cis-retinoic acid | Panretin® | Toctino®
Approved drug PDB Ligand
alitretinoin is an approved drug (FDA (1999), EMA (2000))
Compound class: Metabolite or derivative
Comment: Alitretinoin is an important regulator of gene expression during normal growth and development, as well as in neoplasms. Alitretinoin is a retinoid receptor agonist.
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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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View more information in the IUPHAR Pharmacology Education Project: alitretinoin

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 5
Topological polar surface area 37.3
Molecular weight 300.21
XLogP 6.25
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 CC(=CC=CC(=CC(=O)O)C)C=CC1=C(C)CCCC1(C)C
Isomeric SMILES C/C(=C/C=C/C(=C/C(=O)O)/C)/C=C/C1=C(C)CCCC1(C)C
InChI InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8-,16-14+
InChI Key SHGAZHPCJJPHSC-ZVCIMWCZSA-N
Natural/Endogenous Targets
Target
Retinoid X receptor-α
Retinoid X receptor-β
Retinoid X receptor-γ
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Retinoic acid receptor-α Primary target of this compound Hs Agonist Agonist 9.5 pKd - 3,9
⤷ pKd 9.5 [3,9]
Retinoic acid receptor-γ Primary target of this compound Hs Agonist Agonist 9.0 pKd - 5,9
⤷ pKd 9.0 [5,9]
Retinoic acid receptor-β Primary target of this compound Hs Agonist Agonist 9.7 pKi - 5,9
⤷ pKi 9.7 [5,9]
Retinoid X receptor-α Ligand is endogenous in the given species Hs Agonist Agonist 7.1 – 8.2 pIC50 - 1-2,6-9
⤷ pIC50 7.1 – 8.2 [1-2,6-9]
Retinoid X receptor-β Ligand is endogenous in the given species N/A Agonist Agonist 6.9 – 8.2 pIC50 - 1-2,6-9
⤷ pIC50 6.9 – 8.2 [1-2,6-9]
Retinoid X receptor-γ Ligand is endogenous in the given species Hs Agonist Agonist 7.0 – 8.0 pIC50 - 1-2,6-9
⤷ pIC50 7.0 – 8.0 [1-2,6-9]
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
vitamin K epoxide reductase complex subunit 1 Primary target of this compound Hs Inhibitor Inhibition - - - 4,11
⤷ [4,11]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Rank order of potency at cellular retinoic acid binding protein 1 tretinoin > alitretinoin
stearic acid > palmitic acid, oleic acid, linoleic acid, α-linolenic acid, arachidonic acid 		10
Ligand mentioned in the following text fields
1B. Retinoic acid receptors overview
2B. Retinoid X receptors overview