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.
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 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
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 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
References
1. Bennink HJTC, Bunschoten EJ. (2004)
Pharmaceutical composition comprising estetrol derivatives for use in cancer therapy.
Patent number: WO2004006936A1. Assignee: Pantarhei Biosciences B.V.. Priority date: 12/07/2002. Publication date: 22/01/2004.
2. Coelingh Bennink HJ, Holinka CF, Diczfalusy E. (2008)
Estetrol review: profile and potential clinical applications.
Climacteric, 11 Suppl 1: 47-58. [PMID:18464023]
3. Creinin MD, Westhoff CL, Bouchard C, Chen MJ, Jensen JT, Kaunitz AM, Achilles SL, Foidart JM, Archer DF. (2021)
Estetrol-drospirenone combination oral contraceptive: North American phase 3 efficacy and safety results.
Contraception, 104 (3): 222-228. [PMID:34000251]
4. P K. (2021)
Estetrol and the possibilities of its clinical use.
Ceska Gynekol, 86 (3): 217-221. [PMID:34167315]
5. Visser M, Foidart JM, Coelingh Bennink HJ. (2008)
In vitro effects of estetrol on receptor binding, drug targets and human liver cell metabolism.
Climacteric, 11 Suppl 1: 64-8. [PMID:18464025]