estetrol   Click here for help

GtoPdb Ligand ID: 11591

Synonyms: 15 α-hydroxyestriol | 15 alpha-hydroxyestriol | Drovelis® (EMA); ; estetrol monohydrate + drospirenone | E4 | Lydisilka® (EMA); ; estetrol monohydrate + drospirenone | Nextstellis® (US); estetrol monohydrate + drospirenone
Approved drug PDB Ligand
estetrol is an approved drug (EMA & FDA (2021))
Compound class: Synthetic organic
Comment: Estetrol is a natural estrogen that is produced exclusively during pregnancy by the fetal liver. It is produced synthetically (from a plant source) for medicinal use. Estetrol has tissue selective actions [4-5], with estrogenic activity in the uterus, vagina and endometrium and estrogen antagonist activity in breast tissue.

estetrol is commercially available from our sponsors

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 3
Hydrogen bond donors 4
Rotatable bonds 0
Topological polar surface area 80.92
Molecular weight 304.17
XLogP 2.82
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 Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@@H](O)[C@H]([C@@H]2O)O)C
Isomeric SMILES Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1[C@@H](O)[C@H]([C@@H]2O)O)C
InChI InChI=1S/C18H24O4/c1-18-7-6-12-11-5-3-10(19)8-9(11)2-4-13(12)14(18)15(20)16(21)17(18)22/h3,5,8,12-17,19-22H,2,4,6-7H2,1H3/t12-,13-,14-,15-,16-,17+,18+/m1/s1
InChI Key AJIPIJNNOJSSQC-NYLIRDPKSA-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. EMA (2021)  |  FDA (2021)
IUPAC Name Click here for help
(8R,9S,13S,14S,15R,16R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,15,16,17-tetrol
International Nonproprietary Names Click here for help
INN number INN
10439 estetrol
Synonyms Click here for help
15 α-hydroxyestriol | 15 alpha-hydroxyestriol | Drovelis® (EMA); ; estetrol monohydrate + drospirenone | E4 | Lydisilka® (EMA); ; estetrol monohydrate + drospirenone | Nextstellis® (US); estetrol monohydrate + drospirenone
Database Links Click here for help
BindingDB Ligand 158505
CAS Registry No. 15183-37-6 (source: WHO INN record)
ChEMBL Ligand CHEMBL1230314
DrugBank Ligand DB12235
GtoPdb PubChem SID 442878625
PubChem CID 27125
RCSB PDB Ligand 4OH
Search Google for chemical match using the InChIKey AJIPIJNNOJSSQC-NYLIRDPKSA-N
Search Google for chemicals with the same backbone AJIPIJNNOJSSQC
Search PubMed clinical trials estetrol
Search PubMed titles estetrol
Search PubMed titles/abstracts estetrol
UniChem Compound Search for chemical match using the InChIKey AJIPIJNNOJSSQC-NYLIRDPKSA-N
UniChem Connectivity Search for chemical match using the InChIKey AJIPIJNNOJSSQC-NYLIRDPKSA-N

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MedChemExpress
Estetrol (links to external site)
Cat. No. HY-15731