(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 167388
• Molecular Formular: C22H28F2O5
• Molecular Mass: 410.4515264
• Monoisotopic Mass: 410.19048044
• SMILES: [C@]12([C@H]([C@H]3[C@](C[C@@H]1O)([C@]([C@H](C3)C)(C(=O)CO)O)C)C[C@@H](C1=CC(=O)C=C[C@]21C)F)F
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F)F
• InChI: InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13-,14-,16-,17-,19-,20-,21-,22-/m0/s1
• InChIKey: WXURHACBFYSXBI-XHIJKXOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: apexicon e
• Synonyms: (6α,11β,16β)-6,9-Difluoro-11,17,21-trihydroxy-16-methyl-pregna-1,4-diene-3,20-dione; 6α,9-Difluoro-11β,17,21-trihydroxy-16β-methyl-pregna-1,4-diene-3,20-dione; Diflorasone

Database IDs

• CAS Number: 2557-49-5
• PubChem SID: 162261521
• PubChem CID: 71415

CALCULATED PROPERTIES

• Acid pKa: 12.418192
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.3418503
• LogD (pH = 7.4): 1.3418462
• Log P: 1.3418504
• Molar Refractivity: 102.3163 cm^3
• Polarizability: 39.40079 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Off-White Solid
• Melting Point: 228-239°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D445495

An anti-inflammatory and anti-itching corticosteroid usually present in topical creams.

REFERENCES

• Pedemonte, N., et al.: Am. J. Physiol., 298, C866 (2010)