ethinylestradiol   Click here for help

GtoPdb Ligand ID: 7071

Synonyms: 17α-ethynylestradiol | ethinyl estradiol
Approved drug PDB Ligand
ethinylestradiol is an approved drug
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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2D Structure
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Physico-chemical Properties
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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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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 Model List of Essential Medicines (21st List, 2019). Access PDF version.
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
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Wikipedia Ethinyl estradiol