(1S,2R,10S,11S,14R,15S)-14-ethynyl-15-methyl-17-methylidenetetracyclo[8.7.0.02,7.011,15]heptadec-6-en-14-ol

• ChemBase ID: 173670
• Molecular Formular: C21H28O
• Molecular Mass: 296.44642
• Monoisotopic Mass: 296.21401552
• SMILES: C1CC=C2[C@H](C1)[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=C)([C@@](CC2)(C#C)O)C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC(=C)[C@H]1[C@H]2CCC2=CCCC[C@H]12
• InChI: InChI=1S/C21H28O/c1-4-21(22)12-11-18-17-10-9-15-7-5-6-8-16(15)19(17)14(2)13-20(18,21)3/h1,7,16-19,22H,2,5-6,8-13H2,3H3/t16-,17-,18-,19+,20-,21-/m0/s1
• InChIKey: DKRPZVPROVDZCP-OLGWUGKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-ethynyl-15-methyl-17-methylidenetetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-ol
• IUPAC Traditional name: (1S,2R,10S,11S,14R,15S)-14-ethynyl-15-methyl-17-methylidenetetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-14-ol
• Synonyms: (17α)-11-Methylene-19-norpregn-4-en-20-yn-17-ol; Desogestrel EP Impurity B; 11-Methylenelynestrenol

Database IDs

• CAS Number: 54024-12-3
• PubChem SID: 164229580
• PubChem CID: 71587177

CALCULATED PROPERTIES

• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• Acid pKa: 17.672209
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 3.9760737
• LogD (pH = 7.4): 3.9760737
• Log P: 3.9760737
• Molar Refractivity: 91.1325 cm^3
• Polarizability: 35.560555 Å^3

DETAILS

Toronto Research Chemicals - M304125

11-Methylenelynestrenol is an impurity of the progestogen, Desogestrel (D296875)

REFERENCES

• Van Geerestein, V.J. et al.: Acta Crystallogr. Crys. Struc. Comm., C43, 2232 (1987)