(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-7-en-5-one

• ChemBase ID: 175620
• Molecular Formular: C20H26O2
• Molecular Mass: 298.41924
• Monoisotopic Mass: 298.19328007
• SMILES: C1C(=O)CC2=CC[C@@H]3[C@@H]([C@H]2C1)CC[C@]1([C@H]3CC[C@@]1(O)C#C)C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@@H]1CCC(=O)C2
• InChI: InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,4,15-18,22H,5-12H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
• InChIKey: QGQUHXSBTSDAML-XGXHKTLJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-7-en-5-one
• Synonyms: (17α)-17-Hydroxy-19-norpregn-5-en-20-yn-3-one; 17-Hydroxy-19-nor-17α-pregn-5-en-20-yn-3-one; Δ-5(6)-Norethindrone

Database IDs

• CAS Number: 22933-71-7
• PubChem SID: 164231530
• PubChem CID: 71751195

CALCULATED PROPERTIES

• Acid pKa: 16.378813
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.8574827
• LogD (pH = 7.4): 2.8574827
• Log P: 2.857483
• Molar Refractivity: 87.4478 cm^3
• Polarizability: 34.003754 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N676030

An impurity of Norethindrone Acetate (N675990). One of the Δ5(6)-19-Nor steroids, a new class of potent anabolic agents.

REFERENCES

• Nes, W.R., et al.: Tetrahedron, 19, 299 (1963)