(10S,11S,14R,15S,17R)-14-acetyl-17-[4-(dimethylamino)phenyl]-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-1,6-dien-5-one

• ChemBase ID: 179383
• Molecular Formular: C28H35NO3
• Molecular Mass: 433.5824
• Monoisotopic Mass: 433.26169399
• SMILES: C1C(=O)C=C2C(=C3[C@@H](CC2)[C@H]2[C@](C[C@@H]3c3ccc(cc3)N(C)C)([C@@](CC2)(O)C(=O)C)C)C1
• Canonical SMILES: O=C1CCC2=C3[C@H](C[C@]4([C@H]([C@@H]3CCC2=C1)CC[C@]4(O)C(=O)C)C)c1ccc(cc1)N(C)C
• InChI: InChI=1S/C28H35NO3/c1-17(30)28(32)14-13-25-23-11-7-19-15-21(31)10-12-22(19)26(23)24(16-27(25,28)2)18-5-8-20(9-6-18)29(3)4/h5-6,8-9,15,23-25,32H,7,10-14,16H2,1-4H3/t23-,24+,25-,27-,28-/m0/s1
• InChIKey: HKDLNTKNLJPAIY-WKWWZUSTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,11S,14R,15S,17R)-14-acetyl-17-[4-(dimethylamino)phenyl]-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-5-one
• IUPAC Traditional name: (10S,11S,14R,15S,17R)-14-acetyl-17-[4-(dimethylamino)phenyl]-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-1,6-dien-5-one
• Synonyms: (11β)-11-[4-(Dimethylamino)phenyl]-17-hydroxy-19-norpregna-4,9-diene-3,20-dione; CDB 3236; Deacetyl CDB 2914; Ulipristal

Database IDs

• CAS Number: 159811-51-5
• PubChem SID: 164235293
• PubChem CID: 13559281

CALCULATED PROPERTIES

• Acid pKa: 12.6975355
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.085592
• LogD (pH = 7.4): 4.179422
• Log P: 4.180762
• Molar Refractivity: 129.2858 cm^3
• Polarizability: 49.351673 Å^3
• Polar Surface Area: 57.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - U700800

Ulipristal is a selective progesterone receptor modulator. Ulipristal is used as an emergency contraceptive.

REFERENCES

• Gronemeijer, H., et al.: J. Steroid Biochem., 40, 271 (1991)
• Spitz, I., et al.: Contraception, 48, 403 (1991)
• Conneely, O., et al.: Steroids, 68, 771 (1991)
• Chwalisz, K., et al.: Endocr. Rev., 26, 423 (1991)