(1S,2R,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 178632
• Molecular Formular: C21H28O2
• Molecular Mass: 312.44582
• Monoisotopic Mass: 312.20893014
• SMILES: C1C(=O)C=C2[C@H](C1)[C@@H]1[C@@H]([C@@H](C2)C)[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]2[C@H](C)CC2=CC(=O)CC[C@H]12
• InChI: InChI=1S/C21H28O2/c1-4-21(23)10-8-18-19-13(2)11-14-12-15(22)5-6-16(14)17(19)7-9-20(18,21)3/h1,12-13,16-19,23H,5-11H2,2-3H3/t13-,16+,17-,18+,19-,20+,21+/m1/s1
• InChIKey: WAOKMNBZWBGYIK-KIURNNQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1S,2R,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (7α,17α)-17-Hydroxy-7-methyl-19-norpregn-4-en-20-yn-3-one; 17α-Ethynyl-17-hydroxy-7α-methyl-4-estren-3-one; 7α-Methylnorethindrone; NSC 142228; Org-OM 38; Δ4-Tibolone

Database IDs

• CAS Number: 1162-60-3
• PubChem SID: 164234542
• PubChem CID: 22814761

CALCULATED PROPERTIES

• Acid pKa: 17.594927
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.504247
• LogD (pH = 7.4): 3.504247
• Log P: 3.504247
• Molar Refractivity: 91.9731 cm^3
• Polarizability: 35.84699 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 203-205°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T437505

A metabolite of Tibolone. A synthetic steroid with weak estrogenic, androgenic and progestogenic activity. A pharamceutical used in the treatment of menopausal syndrome.

REFERENCES

• Landgren, M., et al.: Maturitas, 50, 222 (2001)
• Wang, M., et al.: Steroids, 71, 343 (2001)
• Verheul, H., et al.: Drug Metab. Dispos., 35, 1105 (2001)
• Clarkson, T., et al.: J. Clin. Endocrinol. Metab., 86, 5396 (2001)