(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-6-ene-5,8-dione

• ChemBase ID: 176029
• Molecular Formular: C20H24O3
• Molecular Mass: 312.40276
• Monoisotopic Mass: 312.17254463
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2=O)[C@H]2[C@](CC1)([C@](CC2)(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(=O)C2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C20H24O3/c1-3-20(23)9-7-17-15-11-18(22)16-10-12(21)4-5-13(16)14(15)6-8-19(17,20)2/h1,10,13-15,17,23H,4-9,11H2,2H3/t13-,14-,15-,17+,19+,20+/m1/s1
• InChIKey: GFUSEGGPVQNTTK-WLCXVKOPSA-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-6-ene-5,8-dione
• 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-6-ene-5,8-dione
• Synonyms: (17α)-17-Hydroxy-19-norpregn-4-en-20-yne-3,6-dione; 17α-Hydroxy-19-norpregn-4-en-20-yne-3,6-dione; 6-Ketonorethindrone; 6-Oxo Norethindrone

Database IDs

• CAS Number: 67696-78-0
• PubChem SID: 164231939
• PubChem CID: 13828626

CALCULATED PROPERTIES

• Acid pKa: 15.753182
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 2.5499446
• LogD (pH = 7.4): 2.5499446
• Log P: 2.5499446
• Molar Refractivity: 88.1177 cm^3
• Polarizability: 34.077625 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - O858285

An impurity of the progesteron Norethindrone (N676000).

REFERENCES

• Bagocsi, B. et al.: J. Plan. Chrom. Mod. TLC., 16, 359 (2003)
• Gorog, S. et al.: J. Chrom., 400, 177 (2003)