etonogestrel   Click here for help

GtoPdb Ligand ID: 7590

Synonyms: 3-keto-desogestrel | Implanon® | Nexplanon® | ORG-3236
Approved drug
etonogestrel is an approved drug (FDA (2006), EMA (2009))
Compound class: Synthetic organic
Comment: Etonogestrel is the active metabolite of the inactive prodrug desogestrel.
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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 1
Rotatable bonds 1
Topological polar surface area 37.3
Molecular weight 324.21
XLogP 3.4
No. Lipinski's rules broken 0

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 C#CC1(O)CCC2C1(CC)CC(=C)C1C2CCC2=CC(=O)CCC12
Isomeric SMILES C#C[C@]1(O)CC[C@@H]2[C@]1(CC)CC(=C)[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
InChI InChI=1S/C22H28O2/c1-4-21-13-14(3)20-17-9-7-16(23)12-15(17)6-8-18(20)19(21)10-11-22(21,24)5-2/h2,12,17-20,24H,3-4,6-11,13H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
InChI Key GCKFUYQCUCGESZ-BPIQYHPVSA-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. FDA (2006)  |  EMA (2009)
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
Prodrug desogestrel
IUPAC Name Click here for help
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-17-hydroxy-11-methylidene-2,6,7,8,9,10,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
International Nonproprietary Names Click here for help
INN number INN
6832 etonogestrel
Synonyms Click here for help
3-keto-desogestrel | Implanon® | Nexplanon® | ORG-3236
Database Links Click here for help
CAS Registry No. 54048-10-1
ChEBI CHEBI:50777
ChEMBL Ligand CHEMBL1531
DrugBank Ligand DB00294
DrugCentral Ligand 1110
GtoPdb PubChem SID 223365925
PubChem CID 6917715
Search Google for chemical match using the InChIKey GCKFUYQCUCGESZ-BPIQYHPVSA-N
Search Google for chemicals with the same backbone GCKFUYQCUCGESZ
Search PubMed clinical trials etonogestrel
Search PubMed titles etonogestrel
Search PubMed titles/abstracts etonogestrel
UniChem Compound Search for chemical match using the InChIKey GCKFUYQCUCGESZ-BPIQYHPVSA-N
UniChem Connectivity Search for chemical match using the InChIKey GCKFUYQCUCGESZ-BPIQYHPVSA-N
Wikipedia Etonogestrel

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MedChemExpress
Etonogestrel (links to external site)
Cat. No. HY-B0652