2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo(3,3,4,4-2H4)-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.02,9.04,8.013,18]icosane]-14',17'-dien-8'-yl]-2-oxoethyl acetate

• ChemBase ID: 159774
• Molecular Formular: C28H35FO7
• Molecular Mass: 502.5717032
• Monoisotopic Mass: 502.23668168
• 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)COC(=O)C)OC2(O1)CCCC2)C)O)F)C
• Canonical SMILES: CC(=O)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/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1
• InChIKey: ILKJAFIWWBXGDU-MOGDOJJUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo(3,3,4,4-^2H₄)-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-8'-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1'S,2'S,4'R,8'S,9'S,11'S,12'R,13'S)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo(3,3,4,4-^2H₄)-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-8'-yl]-2-oxoethyl acetate
• Synonyms: (11β,16α)-21-(Acetyloxy)-16,17-[cyclopentylidenebis(oxy)]-9-fluoro-11-hydroxypregna-1,4-diene-3,20-dione-d4; Amciderm-d4; Amcinonid-d4; Amcinonide-d4; CL 34699-d4; Cyclocort-d4; Penticort-d4; Visderm-d4; Amcinonide-d4

Database IDs

• PubChem SID: 162253909
• PubChem CID: 71313133

CALCULATED PROPERTIES

• Acid pKa: 13.633899
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.1952636
• LogD (pH = 7.4): 3.1952634
• Log P: 3.1952636
• Molar Refractivity: 127.8767 cm^3
• Polarizability: 50.165337 Å^3
• Polar Surface Area: 99.13 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A576152

Labelled Amcinonide (A576150). Glucocorticoid.

REFERENCES

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