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 hexanoate

• ChemBase ID: 169064
• Molecular Formular: C28H39FO5
• Molecular Mass: 474.6046632
• Monoisotopic Mass: 474.27815257
• 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)CCCCC)C)C)O)F)C
• Canonical SMILES: CCCCCC(=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/C28H39FO5/c1-5-6-7-8-24(33)34-15-23(32)25-16(2)11-19-18-13-21(29)20-12-17(30)9-10-27(20,3)26(18)22(31)14-28(19,25)4/h9-10,12,16,18-19,21-22,25-26,31H,5-8,11,13-15H2,1-4H3/t16-,18+,19+,21+,22+,25-,26-,27+,28+/m1/s1
• InChIKey: WHZRCUIISKRTJL-YTZKRAOUSA-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 hexanoate
• IUPAC Traditional name: fluocortolone caproate
• Synonyms: (6α,11β,16α)-6-Fluoro-11-hydroxy-16-methyl-21-[(1-oxohexyl)oxy]pregna-1,4-diene-3,20-dione; 6α-Fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-Hexanoate; Ficoid; Fluocortolone Caproate; Fluocortolone Hexanoate; Fluorocortolone 21-Caproate; SH 770; Fluocortolone 21-Hexanoate

Database IDs

• CAS Number: 303-40-2
• PubChem SID: 162263196
• PubChem CID: 20054915

CALCULATED PROPERTIES

• Acid pKa: 15.157392
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.4430823
• LogD (pH = 7.4): 4.4430823
• Log P: 4.4430823
• Molar Refractivity: 129.0467 cm^3
• Polarizability: 50.14522 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - F500510

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 (1965)