ulipristal acetate   

GtoPdb Ligand ID: 7460

Synonyms: CDB-2914 | EllaOne® | VA2914
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
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
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
Classification
Compound class Natural product or derivative
Approved drug? Yes (EMA (2009), FDA (2010))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
[(8S,11R,13S,14S,17R)-17-acetyl-11-(4-dimethylaminophenyl)-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate
International Nonproprietary Names
INN number INN
8367 ulipristal
Synonyms
CDB-2914 | EllaOne® | VA2914
Database Links
CAS Registry No. 126784-99-4
ChEBI CHEBI:71025
ChEMBL Ligand CHEMBL260538
DrugCentral Ligand 4166
GtoPdb PubChem SID 187051763
PubChem CID 130904
RCSB PDB Ligand 2S0
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SynPHARM 79767 (in complex with Progesterone receptor)
79768 (in complex with Progesterone receptor)
Wikipedia Ulipristal acetate