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
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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
1. Attardi BJ, Burgenson J, Hild SA, Reel JR. (2004)
In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone.
J Steroid Biochem Mol Biol, 88 (3): 277-88. [PMID:15120421]
2. Rewinkel J, Enthoven M, Golstein I, van der Rijst M, Scholten A, van Tilborg M, de Weys D, Wisse J, Hamersma H. (2008)
11-(pyridinylphenyl)steroids--a new class of mixed-profile progesterone agonists/antagonists.
Bioorg Med Chem, 16 (6): 2753-63. [PMID:18243712]