etretinate   Click here for help

GtoPdb Ligand ID: 7599

Synonyms: Ro-109359 | Tegison®
Approved drug
etretinate is an approved drug (FDA (1986))
Compound class: Synthetic organic
Comment: Etretinate is a highly lipophilic second-generation retinoid. Its use has largely been discontinued as it was discovered to be a long-acting teratogen, with detectable levels in plasma up to three years post-therapy.
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View more information in the IUPHAR Pharmacology Education Project: etretinate

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 0
Rotatable bonds 8
Topological polar surface area 35.53
Molecular weight 354.22
XLogP 6.53
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 CCOC(=O)C=C(C=CC=C(C=Cc1c(C)cc(c(c1C)C)OC)C)C
Isomeric SMILES CCOC(=O)/C=C(/C=C/C=C(/C=C/c1c(C)cc(c(c1C)C)OC)\C)\C
InChI InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
InChI Key HQMNCQVAMBCHCO-DJRRULDNSA-N
Bioactivity Comments
We have been unable to find publicly available affinity data for this drug at its proposed molecular target(s) to substantiate its MMOA, and have therefore not tagged a primary drug target.