(1S,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-14-yl acetate

• ChemBase ID: 175612
• Molecular Formular: C22H28O3
• Molecular Mass: 340.45592
• Monoisotopic Mass: 340.20384476
• SMILES: C1C(=O)CC2=C(C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@@](CC2)(C#C)OC(=O)C)C
• Canonical SMILES: C#C[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=C1CCC(=O)C2)OC(=O)C
• InChI: InChI=1S/C22H28O3/c1-4-22(25-14(2)23)12-10-20-19-7-5-15-13-16(24)6-8-17(15)18(19)9-11-21(20,22)3/h1,18-20H,5-13H2,2-3H3/t18-,19-,20+,21+,22+/m1/s1
• InChIKey: PKMFOAKNKZEDBU-AANPDWTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-14-yl acetate
• IUPAC Traditional name: (1S,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-14-yl acetate
• Synonyms: (17α)-17-(Acetyloxy)-19-norpregn-5(10)-en-20-yn-3-one; 17-Hydroxy-19-Nor-17α-pregn-5(10)-en-20-yn-3-one Acetate; Δ-5(10)-Norethindrone Acetate

Database IDs

• CAS Number: 19637-28-6
• PubChem SID: 164231522
• PubChem CID: 54193985

CALCULATED PROPERTIES

• Acid pKa: 16.301239
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.2549503
• LogD (pH = 7.4): 3.2549503
• Log P: 3.2549503
• Molar Refractivity: 96.3327 cm^3
• Polarizability: 37.83097 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N675995

Norethindrone Acetate (N675990) impurity. Used in studies of progesterone-binding properties of purified uteroglobin-like protein.

REFERENCES

• Beato, M. et al.: J. Reprod. Fert., 53, 305 (1978)
• Schroff, A. P., et al.: Anal. Profiles Drug Subs., 4, 268 (1978)
• Singh, H., et al.: Am. J. Obstet. Gynecol., 135, 409 (1978)