(1S,2S,5S,7S,10R,11S,15S)-5-[(tert-butyldimethylsilyl)oxy]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-14-one

• ChemBase ID: 163336
• Molecular Formular: C25H44O2Si
• Molecular Mass: 404.70116
• Monoisotopic Mass: 404.31105718
• SMILES: C1[C@@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2)[C@H]2[C@](CC1)(C(=O)CC2)C)C)O[Si](C(C)(C)C)(C)C
• Canonical SMILES: O=C1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC[C@@H]2[C@]1(C)CC[C@@H](C2)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C25H44O2Si/c1-23(2,3)28(6,7)27-18-12-14-24(4)17(16-18)8-9-19-20-10-11-22(26)25(20,5)15-13-21(19)24/h17-21H,8-16H2,1-7H3/t17-,18-,19-,20-,21-,24-,25-/m0/s1
• InChIKey: UGWVQACEZWDYMD-YMKPZFJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,5S,7S,10R,11S,15S)-5-[(tert-butyldimethylsilyl)oxy]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-one
• IUPAC Traditional name: (1S,2S,5S,7S,10R,11S,15S)-5-[(tert-butyldimethylsilyl)oxy]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-one
• Synonyms: (3β,5α)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-androstan-17-one; 3β-[(tert-Butyldimethylsilyl)oxy]-17-oxo-5α-androstane; 3β-tert-Butyldimethylsilyloxy Epiandrosterone

Database IDs

• CAS Number: 57711-44-1
• PubChem SID: 162257471
• PubChem CID: 10927608

CALCULATED PROPERTIES

• Acid pKa: 19.96172
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 6.8162
• LogD (pH = 7.4): 6.8162
• Log P: 6.8162
• Molar Refractivity: 113.657 cm^3
• Polarizability: 47.56267 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B691240

Protected Epi Androsterone (E578000). A steroid hormone that is present in normal human urine. Less active 3β-isomer of the androgen Androsterone (A635535). Controlled Substance.

REFERENCES

• Marchand, M., et al.: Eur. J. Biochem., 184, 455 (1989)
• Dardonville, C., et al.: Bioorg. Med. Chem., 11, 3205 (1989)
• Fumarola, L., et al.: Res. Microbiol., 155, 224 (1989)
• Albert, M., et al.: J. Biol. Chem., 280, 28306 (1989)