(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-14-[(trimethylsilyl)oxy]tetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 179253
• Molecular Formular: C23H34O2Si
• Molecular Mass: 370.60036
• Monoisotopic Mass: 370.23280686
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O[Si](C)(C)C)C#C)C
• Canonical SMILES: C#C[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12)O[Si](C)(C)C
• InChI: InChI=1S/C23H34O2Si/c1-6-23(25-26(3,4)5)14-12-21-20-9-7-16-15-17(24)8-10-18(16)19(20)11-13-22(21,23)2/h1,15,18-21H,7-14H2,2-5H3/t18-,19+,20+,21-,22-,23-/m0/s1
• InChIKey: LZECAWNJNIQRQF-GOMYTPFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-14-[(trimethylsilyl)oxy]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-14-[(trimethylsilyl)oxy]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (17α)-17-[(Trimethylsilyl)oxy]-19-norpregn-4-en-20-yn-3-one; 17-(Trimethylsiloxy)-19-nor-17α-pregn-4-en-20-yn-3-one; 17-O-Trimethylsilyl Norethindrone

Database IDs

• CAS Number: 28426-43-9
• PubChem SID: 164235163
• PubChem CID: 14697663

CALCULATED PROPERTIES

• Acid pKa: 19.278301
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.2472
• LogD (pH = 7.4): 5.2472
• Log P: 5.2472
• Molar Refractivity: 103.5504 cm^3
• Polarizability: 42.5359 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform with 5% Methanol; Dichloromethane with 5% Methanol; Dimethyl Sulfoxide; Pyridine
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T796850

Norethindrone (N676000) derivative. Might be a human carcinogen.

REFERENCES

• Schroff, A. P., et al.: Anal. Profiles Drug Subs., 4, 268 (1975)
• Singh, H., et al.: Am. J. Obstet. Gynecol., 135, 409 (1975)
• Toews, M., et al.: Curr. Ther. Res, 41, 509 (1975)