(1S,2R,10S,11S,14R,15S)-14-{2-[(tert-butyldimethylsilyl)oxy]acetyl}-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-5,17-dione

• ChemBase ID: 163434
• Molecular Formular: C27H40O5Si
• Molecular Mass: 472.689
• Monoisotopic Mass: 472.26450091
• SMILES: [C@@H]12[C@H]([C@H]3[C@](CC1=O)([C@@](CC3)(O)C(=O)CO[Si](C(C)(C)C)(C)C)C)CCC1=CC(=O)C=C[C@]21C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@@H]2C(=O)C[C@]2([C@H]1CC[C@]2(O)C(=O)CO[Si](C(C)(C)C)(C)C)C)C
• InChI: InChI=1S/C27H40O5Si/c1-24(2,3)33(6,7)32-16-22(30)27(31)13-11-20-19-9-8-17-14-18(28)10-12-25(17,4)23(19)21(29)15-26(20,27)5/h10,12,14,19-20,23,31H,8-9,11,13,15-16H2,1-7H3/t19-,20-,23+,25-,26-,27-/m0/s1
• InChIKey: BZFJMQRTSOJYLN-FWJOXNLTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,10S,11S,14R,15S)-14-{2-[(tert-butyldimethylsilyl)oxy]acetyl}-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• IUPAC Traditional name: (1S,2R,10S,11S,14R,15S)-14-{2-[(tert-butyldimethylsilyl)oxy]acetyl}-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-5,17-dione
• Synonyms: 21-O-tert-Butyldimethylsilyl Prednisone

Database IDs

• PubChem SID: 162257569
• PubChem CID: 59810485

CALCULATED PROPERTIES

• Acid pKa: 12.606536
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.0783
• LogD (pH = 7.4): 5.078297
• Log P: 5.0783
• Molar Refractivity: 127.4162 cm^3
• Polarizability: 51.529427 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol

DETAILS

Toronto Research Chemicals - B691830

Protected Prednisone (P703780). Adrenocortical steroid. Glucocorticoid, antiinflammatory.

REFERENCES

• Wingerchuk, D., et al.: Neurology, 66, 1485 (2004)
• Fliri, A.F., et al.: J. Med. Chem., 52, 8038 ((2004)
• Lennon, V., et al.: Lancet, 364, 2106 (2004)