2-[(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadecan-14-yl]-2-oxoethyl acetate

• ChemBase ID: 167552
• Molecular Formular: C23H34O6
• Molecular Mass: 406.51246
• Monoisotopic Mass: 406.23553881
• SMILES: C1CC(=O)C[C@@H]2[C@]1([C@@H]1[C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@](CC2)(C(=O)COC(=O)C)O)C)C
• Canonical SMILES: O=C1CC[C@]2([C@@H](C1)CC[C@@H]1[C@@H]2[C@@H](O)C[C@]2([C@H]1CC[C@]2(O)C(=O)COC(=O)C)C)C
• InChI: InChI=1S/C23H34O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h14,16-18,20,26,28H,4-12H2,1-3H3/t14-,16+,17+,18+,20-,21+,22+,23+/m1/s1
• InChIKey: BWCPGWRDUCWIIR-PMBJRREOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2S,7R,10S,11S,14R,15S,17S)-14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-14-yl]-2-oxoethyl acetate
• Synonyms: (5β,11β)-21-(Acetyloxy)-11,17-dihydroxy-pregnane-3,20-dione; 11β,17,21-Trihydroxy-5β-pregnane-3,20-dione 21-Acetate; RU 18760; 5β-Dihydrocortisol 21-Acetate

Database IDs

• CAS Number: 64313-94-6
• PubChem SID: 162261685
• PubChem CID: 71316142

CALCULATED PROPERTIES

• Acid pKa: 12.610284
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7621261
• LogD (pH = 7.4): 1.7621235
• Log P: 1.7621262
• Molar Refractivity: 105.7248 cm^3
• Polarizability: 42.377552 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D448820

Cortisol derivatiove. Shows binding affinities for the cytosol glucocorticoid receptor.

REFERENCES

• Ojasoo, T. et al.; J. Med. Chem. 31, 1160 (1988)