ethinylestradiol   Click here for help

GtoPdb Ligand ID: 7071

Synonyms: 17α-ethynylestradiol | ethinyl estradiol
Approved drug PDB Ligand
ethinylestradiol is an approved drug
Compound class: Metabolite or derivative
Comment: Ethinylestradiol is contained in a large number of combined oral contraceptive formulations and HRT medications. Use of ethinylestradiol, unapposed by a progestin, increases the risk of endometrial cancer.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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View more information in the IUPHAR Pharmacology Education Project: ethinylestradiol

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 1
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 40.46
Molecular weight 296.18
XLogP 4.25
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 C#CC1(O)CCC2C1(C)CCC1C2CCc2c1ccc(c2)O
Isomeric SMILES C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)O
InChI InChI=1S/C20H24O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,5,7,12,16-18,21-22H,4,6,8-11H2,2H3/t16-,17-,18+,19+,20+/m1/s1
InChI Key BFPYWIDHMRZLRN-SLHNCBLASA-N
Classification Click here for help
Compound class Metabolite or derivative
Approved drug? Yes
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 mestranol
IUPAC Name Click here for help
(8R,9S,13S,14S,17R)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
International Nonproprietary Names Click here for help
INN number INN
437 ethinylestradiol
Synonyms Click here for help
17α-ethynylestradiol | ethinyl estradiol
Database Links Click here for help
CAS Registry No. 57-63-6
ChEBI CHEBI:4903
ChEMBL Ligand CHEMBL691
DrugBank Ligand DB00977
DrugCentral Ligand 1082
GtoPdb PubChem SID 178103650
PubChem CID 5991
RCSB PDB Ligand 3WF
Search Google for chemical match using the InChIKey BFPYWIDHMRZLRN-SLHNCBLASA-N
Search Google for chemicals with the same backbone BFPYWIDHMRZLRN
Search PubMed clinical trials ethinylestradiol
Search PubMed titles ethinylestradiol
Search PubMed titles/abstracts ethinylestradiol
UniChem Compound Search for chemical match using the InChIKey BFPYWIDHMRZLRN-SLHNCBLASA-N
UniChem Connectivity Search for chemical match using the InChIKey BFPYWIDHMRZLRN-SLHNCBLASA-N
Wikipedia Ethinyl estradiol