(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5,8-dioxotetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-yl acetate

• ChemBase ID: 176030
• Molecular Formular: C22H26O4
• Molecular Mass: 354.43944
• Monoisotopic Mass: 354.18310931
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2=O)[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]2CC(=O)C2=CC(=O)CC[C@H]12)OC(=O)C
• InChI: InChI=1S/C22H26O4/c1-4-22(26-13(2)23)10-8-19-17-12-20(25)18-11-14(24)5-6-15(18)16(17)7-9-21(19,22)3/h1,11,15-17,19H,5-10,12H2,2-3H3/t15-,16-,17-,19+,21+,22+/m1/s1
• InChIKey: VWZKIXMSPWEBCV-KYPKCDLESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5,8-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5,8-dioxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-yl acetate
• Synonyms: (17α)-17-(Acetyloxy)-19-norpregn-4-en-20-yne-3,6-dione; 6-Ketonorethindrone Acetate; 6-Oxo Norethindrone Acetate

Database IDs

• CAS Number: 438244-27-0
• PubChem SID: 164231940
• PubChem CID: 11428188

CALCULATED PROPERTIES

• Acid pKa: 15.753171
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.99107
• LogD (pH = 7.4): 2.99107
• Log P: 2.99107
• Molar Refractivity: 97.2692 cm^3
• Polarizability: 37.91545 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O858290

An oxidative product of Norethindrone acetate (N675990).

REFERENCES

• Schroff, A.P., et al.: Anal. Profiles Drug Subs., 4, 268 (1975)
• Singh, H., et al.: Am. J. Obstet. Gynecol., 135, 409 (1979)