[(1S,5R,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-2(7)-en-5-yl]oxidanesulfonic acid

• ChemBase ID: 178024
• Molecular Formular: C21H30O5S
• Molecular Mass: 394.5249
• Monoisotopic Mass: 394.18139506
• SMILES: C1[C@H](CC2=C(C1)[C@@H]1[C@@H]([C@@H](C2)C)[C@H]2[C@](CC1)([C@](CC2)(O)C#C)C)OS(=O)(=O)O
• 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=C1CC[C@H](C2)OS(=O)(=O)O
• InChI: InChI=1S/C21H30O5S/c1-4-21(22)10-8-18-19-13(2)11-14-12-15(26-27(23,24)25)5-6-16(14)17(19)7-9-20(18,21)3/h1,13,15,17-19,22H,5-12H2,2-3H3,(H,23,24,25)/t13-,15-,17-,18+,19-,20+,21+/m1/s1
• InChIKey: AEMPRRLENKOPGQ-CZTKNSHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(1S,5R,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-5-yl]oxidanesulfonic acid
• IUPAC Traditional name: [(1S,5R,9R,10R,11S,14R,15S)-14-ethynyl-14-hydroxy-9,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-2(7)-en-5-yl]oxidanesulfonic acid
• Synonyms: (3α,7α,17α)-7-Methyl-19-norpregn-5(10)-en-20-yne-3,17-diol 3-(Hydrogen Sulfate); 3α-Sulfooxy Tibolone

Database IDs

• CAS Number: 144466-06-8
• PubChem SID: 164233934
• PubChem CID: 11176885

CALCULATED PROPERTIES

• Acid pKa: -1.1870159
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.5719443
• LogD (pH = 7.4): 0.5719304
• Log P: 1.5984752
• Molar Refractivity: 102.7497 cm^3
• Polarizability: 41.117153 Å^3
• Polar Surface Area: 83.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - S733700

3α-Hydroxy Tibolone 17-O-Sulfate is the 3-sulfate conjugate of 3α-Hydroxy Tibolone and a metabolite of Tibolone (T437500), a synthetic steroid used in the treatment of menopausal syndrome.

REFERENCES

• Verheul, H.A.M. et al.: Drug Metab. Dispos., 35, 1112 (2007)
• Vos, R.M.E. et al.: Drug Metab. Dispos., 30, 106 (2007)
• Verhoeven, C.H.J. et al.: Eur. J. Drug Metab. Pharmacokin., 27, 1 (2007)