(1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-14-yl acetate

• ChemBase ID: 165662
• Molecular Formular: C22H26O3
• Molecular Mass: 338.44004
• Monoisotopic Mass: 338.18819469
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](C=C2)[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]2C=CC2=CC(=O)CC[C@H]12)OC(=O)C
• InChI: InChI=1S/C22H26O3/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/h1,5,7,13,17-20H,6,8-12H2,2-3H3/t17-,18+,19+,20-,21-,22-/m0/s1
• InChIKey: DQSVONCNGQQILU-ZCPXKWAGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-15-methyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• Synonyms: 17-Hydroxy-19-Nor-17α-pregna-4,6-dien-20-yn-3-one Acetate; Δ-6(7)-Norenthindrone Acetate; 6,7-Dehydro Norethindrone Acetate

Database IDs

• CAS Number: 106765-04-2
• PubChem SID: 162259795
• PubChem CID: 3065098

CALCULATED PROPERTIES

• Acid pKa: 19.691463
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.2964318
• LogD (pH = 7.4): 3.2964318
• Log P: 3.2964318
• Molar Refractivity: 97.6926 cm^3
• Polarizability: 37.589424 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229905

An acetoxyprogesterone derivative of Norethindrone acetate (N675990). Used in comparison study of progestational activity with norethyltestosterone.

REFERENCES

• Kincl, F.A.: Endokrinologie, 40, 257 (1961)
• Schroff, A. P., et al.: Anal. Profiles Drug Subs., 4, 268 (1961)
• Singh, H., et al.: Am. J. Obstet. Gynecol., 135, 409 (1979)