(1S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-2(7),3,5-trien-5-yl acetate

• ChemBase ID: 168073
• Molecular Formular: C22H26O3
• Molecular Mass: 338.44004
• Monoisotopic Mass: 338.18819469
• SMILES: c1cc(cc2c1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)OC(=O)C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCc2c1ccc(c2)OC(=O)C
• InChI: InChI=1S/C22H26O3/c1-4-22(24)12-10-20-19-7-5-15-13-16(25-14(2)23)6-8-17(15)18(19)9-11-21(20,22)3/h1,6,8,13,18-20,24H,5,7,9-12H2,2-3H3/t18-,19-,20+,21+,22+/m1/s1
• InChIKey: WHONTIANOSNSAH-AANPDWTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-5-yl acetate
• IUPAC Traditional name: (1S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-2(7),3,5-trien-5-yl acetate
• Synonyms: (17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol 3-Acetate; 19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17-diol 3-Acetate; Ethynyl Estradiol 3-Acetate

Database IDs

• CAS Number: 5779-47-5
• PubChem SID: 162262205
• PubChem CID: 22790936

CALCULATED PROPERTIES

• Acid pKa: 17.59492
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.8081794
• LogD (pH = 7.4): 3.8081794
• Log P: 3.8081794
• Molar Refractivity: 96.526 cm^3
• Polarizability: 37.71367 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - E685125

A synthetic steroid with potential use as an oral contraceptive.

REFERENCES

• Evans, R., et al.: Science, 240, 889 (1988)
• Napolitano, E., et al.: J. Med. Chem., 34, 2754 (1988)
• Hart, L., et al.: Biochem. Cell Biol., 80, 335 (1988)