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

• ChemBase ID: 166608
• Molecular Formular: C27H33NO3
• Molecular Mass: 419.55582
• Monoisotopic Mass: 419.24604392
• SMILES: C1C(=O)C=C2C(=C3[C@@H](CC2)[C@H]2[C@](C[C@@H]3c3ccc(cc3)NC)([C@@](CC2)(O)C(=O)C)C)C1
• Canonical SMILES: CNc1ccc(cc1)[C@H]1C[C@@]2(C)[C@H]([C@H]3C1=C1CCC(=O)C=C1CC3)CC[C@]2(O)C(=O)C
• InChI: InChI=1S/C27H33NO3/c1-16(29)27(31)13-12-24-22-10-6-18-14-20(30)9-11-21(18)25(22)23(15-26(24,27)2)17-4-7-19(28-3)8-5-17/h4-5,7-8,14,22-24,28,31H,6,9-13,15H2,1-3H3/t22-,23+,24-,26-,27-/m0/s1
• InChIKey: YRFSIKXKDZSLPG-YEEPMTPTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (10S,11S,14R,15S,17R)-14-acetyl-14-hydroxy-15-methyl-17-[4-(methylamino)phenyl]tetracyclo[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-14-hydroxy-15-methyl-17-[4-(methylamino)phenyl]tetracyclo[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-d3; Deacetyl CDB 2914-d3; Ulipristal-d3; (11β)-17-Hydroxy-11-[4-(methylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione; N-Desmethyl Ulipristal

Database IDs

• CAS Number: 159681-67-1
• PubChem SID: 162260741
• PubChem CID: 15908062

CALCULATED PROPERTIES

• Acid pKa: 12.6975355
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.4895942
• LogD (pH = 7.4): 3.544743
• Log P: 3.545496
• Molar Refractivity: 125.051 cm^3
• Polarizability: 47.509113 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D296000

A metabolite of Ulipristal.

Toronto Research Chemicals - U700802

Labelled Ulipristal (U700800). Ulipristal is a selective progesterone receptor modulator. Ulipristal is used during pregnancy.

REFERENCES

• Heikinheimo, O., et al.: J. Steroid Biochem., 26, 279 (1987)
• Bock, H., et al.: Chem. Ber., 127, 55 (1987)
• Teutsch, G., et al.: Steroids, 59, 22 (1987)
• 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)