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

• ChemBase ID: 175611
• Molecular Formular: C20H26O2
• Molecular Mass: 298.41924
• Monoisotopic Mass: 298.19328007
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](CC2)[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]2CCC2=CC(=O)CC[C@H]12
• 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/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20+/m0/s1
• InChIKey: VIKNJXKGJWUCNN-JBKQDOAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14S,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14S,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: 17-Hydroxy-19-norpregn-4-en-20-yn-3-one; 18-Methyllevonorgestrel; 17-epi-Norethindrone

Database IDs

• CAS Number: 38673-36-8
• PubChem SID: 164231521
• PubChem CID: 9839243

CALCULATED PROPERTIES

• Acid pKa: 17.594933
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.217228
• LogD (pH = 7.4): 3.217228
• Log P: 3.217228
• Molar Refractivity: 87.4245 cm^3
• Polarizability: 34.003754 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 216-219°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N675985

Norethindrone (N676000) epimer. Norethindrone and acetate is used in combination with estrogen as contraceptive (oral).

REFERENCES

• Angel, P., et al.: Biochim. Biophys. Acta., 1072, 129 (1991)
• Chenu, C., et al.: J. Cell Biol., 127, 1149 (1991)
• Schmidt, M., et al.: J. Endocrinol., 158, 401 (1991)