ulipristal acetate   Click here for help

GtoPdb Ligand ID: 7460

Synonyms: CDB-2914 | EllaOne® | VA2914
Approved drug PDB Ligand
ulipristal acetate is an approved drug (EMA (2009), FDA (2010))
Comment: Ulipristal acetate is a selective progesterone receptor modulator (SPRM) contained in certain emergency contraceptives.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 5
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 63.68
Molecular weight 475.27
XLogP 4.18
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(=O)OC1(CCC2C1(C)CC(c1ccc(cc1)N(C)C)C1=C3CCC(=O)C=C3CCC21)C(=O)C
Isomeric SMILES CC(=O)O[C@@]1(CC[C@@H]2[C@]1(C)C[C@H](c1ccc(cc1)N(C)C)C1=C3CCC(=O)C=C3CC[C@@H]21)C(=O)C
InChI InChI=1S/C30H37NO4/c1-18(32)30(35-19(2)33)15-14-27-25-12-8-21-16-23(34)11-13-24(21)28(25)26(17-29(27,30)3)20-6-9-22(10-7-20)31(4)5/h6-7,9-10,16,25-27H,8,11-15,17H2,1-5H3/t25-,26+,27-,29-,30-/m0/s1
InChI Key OOLLAFOLCSJHRE-ZHAKMVSLSA-N
Selectivity at nuclear hormone receptors
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Progesterone receptor Primary target of this compound Hs Agonist Partial agonist <7.0 pEC50 - 2
pEC50 <7.0 (EC50 >1x10-7 M) [2]
Progesterone receptor Primary target of this compound Hs Antagonist Antagonist 9.7 pIC50 - 2
pIC50 9.7 (IC50 2x10-10 M) [2]