(1S,9R,10R,11S,14R,15S)-14-ethynyl-5,5-dimethoxy-9,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-14-ol

• ChemBase ID: 178634
• Molecular Formular: C23H34O3
• Molecular Mass: 358.51426
• Monoisotopic Mass: 358.25079495
• SMILES: C1C(CC2=C(C1)[C@@H]1[C@@H]([C@@H](C2)C)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)(OC)OC
• Canonical SMILES: COC1(OC)CCC2=C(C1)C[C@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@]2(O)C#C)C)C
• InChI: InChI=1S/C23H34O3/c1-6-22(24)11-9-19-20-15(2)13-16-14-23(25-4,26-5)12-8-17(16)18(20)7-10-21(19,22)3/h1,15,18-20,24H,7-14H2,2-5H3/t15-,18-,19+,20-,21+,22+/m1/s1
• InChIKey: UELCQPZSOLYWMG-LADQHVHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,9R,10R,11S,14R,15S)-14-ethynyl-5,5-dimethoxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-14-ol
• IUPAC Traditional name: (1S,9R,10R,11S,14R,15S)-14-ethynyl-5,5-dimethoxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-14-ol
• Synonyms: (7α,17α)-3,3-Dimethoxy-7-methyl-19-norpregn-5(10)-en-20-yn-17-ol; Tibolone 3-Dimethyl Ketal

Database IDs

• CAS Number: 105186-33-2
• PubChem SID: 164234544
• PubChem CID: 71752566

CALCULATED PROPERTIES

• Acid pKa: 17.594913
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 3.5325093
• LogD (pH = 7.4): 3.5325093
• Log P: 3.5325093
• Molar Refractivity: 103.9484 cm^3
• Polarizability: 40.839405 Å^3
• Polar Surface Area: 38.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T437515

Tibolone intermediate.

REFERENCES

• Wieland, P., et al.: Helv. Chim. Acta, 50, 1453 (1967)
• Funke, C.W., et al.: J. Labelled Comp. Radiopharm., 20, 843 (1967)