(1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-5-one

• ChemBase ID: 165664
• Molecular Formular: C20H24O2
• Molecular Mass: 296.40336
• Monoisotopic Mass: 296.17763001
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H](C=C2)[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]2C=CC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C20H24O2/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/h1,4,6,12,15-18,22H,5,7-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
• InChIKey: SWNFRSGMYREPFG-XGXHKTLJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-5-one
• IUPAC Traditional name: (1S,2R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-15-methyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-5-one
• Synonyms: (17α)-17-Hydroxy-19-norpregna-4,6-dien-20-yn-3-one; 17-Hydroxy-19-nor-17α-pregna-4,6-dien-20-yn-3-one; 7α-Ethynyl-17β-hydroxyestra-4,6-dien-3-one; 6,7-Dehydronorethindrone; 6,7-Dehydro Norethindrone

Database IDs

• CAS Number: 31528-46-8
• PubChem SID: 162259797
• PubChem CID: 22216246

CALCULATED PROPERTIES

• Acid pKa: 17.661785
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.8553061
• LogD (pH = 7.4): 2.8553064
• Log P: 2.8553064
• Molar Refractivity: 88.5411 cm^3
• Polarizability: 33.76406 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D229915

Norethindrone (N676000) derivative with progestational and antiestrogenic activities

REFERENCES

• Gilbert, H.G. et al.: Steroids, 23, 585 (1974)