2-[(1S,2R,8S,10S,11S,13R,14S,15S,17S)-8-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 169063
• Molecular Formular: C24H31FO5
• Molecular Mass: 418.4983432
• Monoisotopic Mass: 418.21555231
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@H]2[C@H](C[C@]2([C@H]1C[C@H]([C@@H]2C(=O)COC(=O)C)C)C)O)F)C
• Canonical SMILES: CC(=O)OCC(=O)[C@H]1[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C24H31FO5/c1-12-7-16-15-9-18(25)17-8-14(27)5-6-23(17,3)22(15)19(28)10-24(16,4)21(12)20(29)11-30-13(2)26/h5-6,8,12,15-16,18-19,21-22,28H,7,9-11H2,1-4H3/t12-,15+,16+,18+,19+,21-,22-,23+,24+/m1/s1
• InChIKey: VLHRIOASVODQEX-WLDNQIQOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2R,8S,10S,11S,13R,14S,15S,17S)-8-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2R,8S,10S,11S,13R,14S,15S,17S)-8-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• Synonyms: 21-Acetoxy-6α-fluoro-11β-hydroxy-16α-methylpregna-1,4-diene-3,20-dione; 21-Acetoxyfluocortolone; (6α,11β,16α)-21-(Acetyloxy)-6-fluoro-11-hydroxy-16-methyl-pregna-1,4-diene-3,20-dione; Fluocortolone Acetate

Database IDs

• CAS Number: 1176-82-5
• PubChem SID: 162263195
• PubChem CID: 22798516

CALCULATED PROPERTIES

• Acid pKa: 15.15738
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.408841
• LogD (pH = 7.4): 2.4088402
• Log P: 2.4088402
• Molar Refractivity: 110.6168 cm^3
• Polarizability: 42.80963 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Light Yellow Solid

DETAILS

Toronto Research Chemicals - F500505

Fluocortolone (F500500) derivative. Glucocorticoid.

REFERENCES

• Breuer, et al.: Arzneim.-Forsch., 15, 50 (1965)
• Domenico, et al.: Arzneim.-Forsch., 15, 46 (1965)
• Gerhards, et al.: Acta Endocrinol., 68, 98 (1971)