desogestrel   Click here for help

GtoPdb Ligand ID: 7065

Synonyms: ORG-2969
Approved drug
desogestrel is an approved drug (FDA (1992), EMA (1998))
Compound class: Synthetic organic
Comment: Desogestrel is a progestin (synthetic progesterone-like agent) widely used in third-generation hormonal contraceptives. Desogestrel is converted to etonogestrel (3-ketodesogestrel) in vivo. There has been controversy surrounding reports that third-generation oral contraceptives containing desogestrel pose a risk of dangerous blood clots compared to older second-generation oral contraceptives.
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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 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 20.23
Molecular weight 310.23
XLogP 5.49
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 CCC12CC(=C)C3C(C1CCC2(O)C#C)CCC1=CCCCC31
Isomeric SMILES CC[C@]12CC(=C)[C@H]3[C@H]([C@@H]1CC[C@@]2(O)C#C)CCC1=CCCC[C@H]31
InChI InChI=1S/C22H30O/c1-4-21-14-15(3)20-17-9-7-6-8-16(17)10-11-18(20)19(21)12-13-22(21,23)5-2/h2,8,17-20,23H,3-4,6-7,9-14H2,1H3/t17-,18-,19-,20+,21-,22-/m0/s1
InChI Key RPLCPCMSCLEKRS-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 (1992)  |  EMA (1998)
Is prodrug? Yes
Active form etonogestrel
IUPAC Name Click here for help
(8S,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-11-methylidene-1,2,3,6,7,8,9,10,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-ol
International Nonproprietary Names Click here for help
INN number INN
4384 desogestrel
Synonyms Click here for help
ORG-2969
Database Links Click here for help
CAS Registry No. 54024-22-5
ChEMBL Ligand CHEMBL1533
DrugBank Ligand DB00304
DrugCentral Ligand 818
GtoPdb PubChem SID 178103644
LIPID MAPS LMST02030104
PubChem CID 40973
Search Google for chemical match using the InChIKey RPLCPCMSCLEKRS-BPIQYHPVSA-N
Search Google for chemicals with the same backbone RPLCPCMSCLEKRS
Search PubMed clinical trials desogestrel
Search PubMed titles desogestrel
Search PubMed titles/abstracts desogestrel
UniChem Compound Search for chemical match using the InChIKey RPLCPCMSCLEKRS-BPIQYHPVSA-N
UniChem Connectivity Search for chemical match using the InChIKey RPLCPCMSCLEKRS-BPIQYHPVSA-N
Wikipedia Desogestrel

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MedChemExpress
Desogestrel (links to external site)
Cat. No. HY-12516