(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-8'-(2-hydroxyacetyl)-9',13'-dimethyl-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosane]-14',17'-dien-16'-one

• ChemBase ID: 166045
• Molecular Formular: C26H33FO6
• Molecular Mass: 460.5350232
• Monoisotopic Mass: 460.226117
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]1[C@@]2(C(=O)CO)OC2(O1)CCCC2)C)O)F)C
• Canonical SMILES: OCC(=O)[C@@]12OC3(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1CCC1=CC(=O)C=C[C@]21C)F)CCCC3
• InChI: InChI=1S/C26H33FO6/c1-22-10-7-16(29)11-15(22)5-6-17-18-12-21-26(20(31)14-28,33-24(32-21)8-3-4-9-24)23(18,2)13-19(30)25(17,22)27/h7,10-11,17-19,21,28,30H,3-6,8-9,12-14H2,1-2H3/t17-,18-,19-,21+,22-,23-,25-,26+/m0/s1
• InChIKey: FLDUYPKFSAAGBK-LFZVSNMSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-8'-(2-hydroxyacetyl)-9',13'-dimethyl-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosane]-14',17'-dien-16'-one
• IUPAC Traditional name: (1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-8'-(2-hydroxyacetyl)-9',13'-dimethyl-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosane]-14',17'-dien-16'-one
• Synonyms: (11β,16α)-16,17-[Cyclopentylidenebis(oxy)]-9-fluoro-11,21-dihydroxypregna-1,4-diene-3,20-dione; 21-Desacetyl Amcinonide

Database IDs

• CAS Number: 55646-99-6
• PubChem SID: 162260178
• PubChem CID: 71315526

CALCULATED PROPERTIES

• Acid pKa: 13.40196
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.7541382
• LogD (pH = 7.4): 2.7541378
• Log P: 2.7541382
• Molar Refractivity: 118.7252 cm^3
• Polarizability: 46.312664 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D288380

Amcinonide (A576150) analog as glucocorticoid receptor agonists for the treatment of inflammation and allergic conditions.

REFERENCES

• Woodford, R., et al.: Curr. Ther. Res., 26, 301 (1979)