mifepristone   

GtoPdb Ligand ID: 2805

Synonyms: Mifeprex® | RU-486 | RU486
mifepristone is an approved drug (FDA (2000))
Compound class: Synthetic organic
Comment: An antagonist of both the glucocorticoid receptor and the progesterone receptor.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 40.54
Molecular weight 429.27
XLogP 4.66
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CC#CC1(O)CCC2C1(C)CC(c1ccc(cc1)N(C)C)C1=C3CCC(=O)C=C3CCC21
Isomeric SMILES CC#C[C@]1(O)CC[C@@H]2[C@]1(C)C[C@H](c1ccc(cc1)N(C)C)C1=C3CCC(=O)C=C3CC[C@@H]21
InChI InChI=1S/C29H35NO2/c1-5-15-29(32)16-14-26-24-12-8-20-17-22(31)11-13-23(20)27(24)25(18-28(26,29)2)19-6-9-21(10-7-19)30(3)4/h6-7,9-10,17,24-26,32H,8,11-14,16,18H2,1-4H3/t24-,25+,26-,28-,29-/m0/s1
InChI Key VKHAHZOOUSRJNA-GCNJZUOMSA-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
Glucocorticoid receptor Hs Antagonist Antagonist 9.4 pKd - 1,3
pKd 9.4 [1,3]
Androgen receptor Hs Antagonist Antagonist 9.2 pKi - 4
pKi 9.2 (Ki 6.5x10-10 M) [4]
Progesterone receptor Hs Agonist Mixed 9.0 pKi - 5
pKi 9.0 (Ki 1.1x10-9 M) [5]
Progesterone receptor Hs Antagonist Mixed 9.0 pKi - 5
pKi 9.0 (Ki 1.1x10-9 M) [5]
Pregnane X receptor Hs Agonist Agonist ~5.0 pEC50 - 2
pEC50 ~5.0 (EC50 ~1x10-5 M) [2]