(1S,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-methoxytetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-14-ol

• ChemBase ID: 173896
• Molecular Formular: C22H28O2
• Molecular Mass: 324.45652
• Monoisotopic Mass: 324.20893014
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)CC)OC
• Canonical SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@]2(O)C#C)CCc1c3ccc(c1)OC
• InChI: InChI=1S/C22H28O2/c1-4-21-12-10-18-17-9-7-16(24-3)14-15(17)6-8-19(18)20(21)11-13-22(21,23)5-2/h2,7,9,14,18-20,23H,4,6,8,10-13H2,1,3H3/t18-,19-,20+,21+,22+/m1/s1
• InChIKey: NXKYEZGQCNWQRT-AANPDWTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-methoxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-14-ol
• IUPAC Traditional name: (1S,10R,11S,14R,15S)-15-ethyl-14-ethynyl-5-methoxytetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-14-ol
• Synonyms: (17α)-13-Ethyl-3-methoxy-18,19-dinorpregna-1,3,5(10)-trien-20-yn-17-ol; 13β-Ethyl-17α-ethynyl-3-methoxyestra-1,3,5(10)-trien-17β-ol; 18-Methyl Mestranol

Database IDs

• CAS Number: 14009-70-2
• PubChem SID: 164229806
• PubChem CID: 22790399

CALCULATED PROPERTIES

• Acid pKa: 17.909277
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 4.487816
• LogD (pH = 7.4): 4.487816
• Log P: 4.487816
• Molar Refractivity: 96.4578 cm^3
• Polarizability: 37.657867 Å^3
• Polar Surface Area: 29.46 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M320275

Mestranol (M258755) derivative. It is used as contraceptive.

REFERENCES

• Cullen, L.F., et al.: J. Pharma. Sci., 57, 1857 (1968)