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
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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Click here for structure editor
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 5
Topological polar surface area 37.3
Molecular weight 300.21
XLogP 6.25
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 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

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 Metabolite
Approved drug? Yes (FDA (1999), EMA (2000))
IUPAC Name Click here for help
(2E,4E,6Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic acid
International Nonproprietary Names Click here for help
INN number INN
7781 alitretinoin
Synonyms Click here for help
9-cis-retinoic acid | Panretin® | Toctino®
Database Links Click here for help
BindingDB Ligand 31892
CAS Registry No. 5300-03-8 (source: Scifinder)
ChEBI CHEBI:50648
ChEMBL Ligand CHEMBL705
DrugBank Ligand DB00523
DrugCentral Ligand 3862
GtoPdb PubChem SID 135651418
LIPID MAPS LMPR01090022
PubChem CID 449171
RCSB PDB Ligand 9CR
Search Google for chemical match using the InChIKey SHGAZHPCJJPHSC-ZVCIMWCZSA-N
Search Google for chemicals with the same backbone SHGAZHPCJJPHSC
Search PubMed clinical trials alitretinoin
Search PubMed titles alitretinoin
Search PubMed titles/abstracts alitretinoin
SynPHARM 6485 (in complex with Retinoid X receptor-α)
UniChem Compound Search for chemical match using the InChIKey SHGAZHPCJJPHSC-ZVCIMWCZSA-N
UniChem Connectivity Search for chemical match using the InChIKey SHGAZHPCJJPHSC-ZVCIMWCZSA-N
Wikipedia Alitretinoin