(10S,11S,14S,15S,17R)-14-hydroxy-15-methyl-17-{4-[(2H3)methyl(methyl)amino]phenyl}-14-(prop-1-yn-1-yl)tetracyclo[8.7.0.02,7.011,15]heptadeca-1,6-dien-5-one

• ChemBase ID: 174626
• Molecular Formular: C29H35NO2
• Molecular Mass: 429.5937
• Monoisotopic Mass: 429.26677937
• SMILES: C1CC(=O)C=C2C1=C1[C@@H](CC2)[C@H]2[C@](C[C@@H]1c1ccc(cc1)N(C)C)([C@](CC2)(O)C#CC)C
• Canonical 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
• InChIKey: VKHAHZOOUSRJNA-GCNJZUOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,11S,14S,15S,17R)-14-hydroxy-15-methyl-17-{4-[(^2H₃)methyl(methyl)amino]phenyl}-14-(prop-1-yn-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-5-one
• IUPAC Traditional name: (10S,11S,14S,15S,17R)-14-hydroxy-15-methyl-17-{4-[(^2H₃)methyl(methyl)amino]phenyl}-14-(prop-1-yn-1-yl)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-5-one
• Synonyms: (11β,17β)-11-[4-(Dimethylamino-d3)phenyl]-17-hydroxy-17-(1-propyn-1-yl)estra-4,9-dien-3-one; RU-486-d3; RU-38486-d3; Mifegyne-d3; Mifeprex-d3; Mifestone-d3; VGX 410-d3; Mifepristone-d3

Database IDs

• PubChem SID: 164230536
• PubChem CID: 46782374

CALCULATED PROPERTIES

• Acid pKa: 12.865694
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 5.038118
• LogD (pH = 7.4): 5.1319485
• Log P: 5.1332874
• Molar Refractivity: 132.5809 cm^3
• Polarizability: 50.04145 Å^3
• Polar Surface Area: 40.54 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 74-76°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M343977

A labelled progesterone receptor antagonist with partial agonist activity. Abortifacient.

REFERENCES

• Healy, D.L., et al.: J. Clin. Endocrinol. Metab., 57, 863 (1983)
• Rauch, M., et al.: Eur. J. Biochem., 148, 213 (1983)
• Baulieu, E.E., et al.: Science, 245, 1351 (1983)
• Brogden, R.N., et al.: Drugs, 45, 384 (1993)