(1S,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-5-one

• ChemBase ID: 175618
• Molecular Formular: C20H26O2
• Molecular Mass: 298.41924
• Monoisotopic Mass: 298.19328007
• SMILES: C1C(=O)CC2=C(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=C1CCC(=O)C2
• 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/h1,16-18,22H,4-12H2,2H3/t16-,17-,18+,19+,20+/m1/s1
• InChIKey: ICTXHFFSOAJUMG-SLHNCBLASA-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]heptadec-2(7)-en-5-one
• IUPAC Traditional name: norethynodrel
• Synonyms: 13-Methyl-17-ethynyl-17-hydroxy-1,2,3,4,6,7,8,9,11,12,13,14,16,17-tetradecahydro-15H-cyclopenta[a]phenanthren-3-one; 17-Hydroxy-19-nor-17α-pregn-5(10)-en-20-yn-3-one; (17α)-17-hydroxy-19-Norpregn-5(10)-en-20-yn-3-one; Norethynodrel

Database IDs

• CAS Number: 68-23-5
• PubChem SID: 164231528
• PubChem CID: 6231

CALCULATED PROPERTIES

• Acid pKa: 16.301239
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.813825
• LogD (pH = 7.4): 2.813825
• Log P: 2.813825
• Molar Refractivity: 87.1812 cm^3
• Polarizability: 34.003754 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N676020

The compound is a progestin used in Enovid, an oral contraceptive, also used in the treatment of endometriosis and hypermenorrhea.

REFERENCES

• Palmer K., et al.: J. Pharmacol. Exp. Ther., 167, 207 (1969)
• Liu, L., et al.: Endocrinology., 151, 5782 (1969)
• Sonneveld, E., et al.: Toxicol. in Vitro, 25, 545 (2011)