(1S,2R,10S,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyl-17-methylidenetetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 165759
• Molecular Formular: C21H26O2
• Molecular Mass: 310.42994
• Monoisotopic Mass: 310.19328007
• SMILES: C1CC(=O)C=C2[C@H]1[C@@H]1[C@@H](CC2)[C@H]2[C@](CC1=C)([C@](CC2)(O)C#C)C
• Canonical SMILES: C#C[C@]1(O)CC[C@@H]2[C@]1(C)CC(=C)[C@H]1[C@H]2CCC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C21H26O2/c1-4-21(23)10-9-18-17-7-5-14-11-15(22)6-8-16(14)19(17)13(2)12-20(18,21)3/h1,11,16-19,23H,2,5-10,12H2,3H3/t16-,17-,18-,19+,20-,21-/m0/s1
• InChIKey: VBLPWTJRPURMLR-OLGWUGKESA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 54024-10-1
• PubChem SID: 162259892
• PubChem CID: 21680464

CALCULATED PROPERTIES

• Acid pKa: 17.672209
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.1566012
• LogD (pH = 7.4): 3.1566012
• Log P: 3.1566012
• Molar Refractivity: 91.7506 cm^3
• Polarizability: 35.607704 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230940

Etonogestrel derivative, a contraceptive progestins.

REFERENCES

• Bergink, E., et al.: J. Steroid. Biochem., 19, 1563 (1983)
• Van der Vies, J., et al.: Arzneim.-Forsch., 33, 231 (1983)
• Killinger, J., et al.: Contraception, 32, 311 (1983)