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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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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 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 0
Rotatable bonds 8
Topological polar surface area 35.53
Molecular weight 354.22
XLogP 6.53
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 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

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 Synthetic organic
Approved drug? Yes. US FDA (1986)
Withdrawn drug? Yes
IUPAC Name Click here for help
ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
International Nonproprietary Names Click here for help
INN number INN
4658 etretinate
Synonyms Click here for help
Ro-109359 | Tegison®
Database Links Click here for help
CAS Registry No. 54350-48-0
ChEMBL Ligand CHEMBL464
DrugBank Ligand DB00926
DrugCentral Ligand 1116
GtoPdb PubChem SID 223365934
LIPID MAPS LMPR01090046
PubChem CID 5282375
Search Google for chemical match using the InChIKey HQMNCQVAMBCHCO-DJRRULDNSA-N
Search Google for chemicals with the same backbone HQMNCQVAMBCHCO
Search PubMed clinical trials etretinate
Search PubMed titles etretinate
Search PubMed titles/abstracts etretinate
UniChem Compound Search for chemical match using the InChIKey HQMNCQVAMBCHCO-DJRRULDNSA-N
UniChem Connectivity Search for chemical match using the InChIKey HQMNCQVAMBCHCO-DJRRULDNSA-N
Wikipedia Etretinate

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MedChemExpress
Etretinate (links to external site)
Cat. No. HY-B0797