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

• ChemBase ID: 159398
• Molecular Formular: C24H30F2O6
• Molecular Mass: 452.4882064
• Monoisotopic Mass: 452.20104512
• SMILES: [C@]12([C@@H](C[C@@H](C3=CC(=O)C=C[C@]23C)F)[C@H]2[C@](C[C@@H]1O)([C@]([C@H](C2)C)(C(=O)COC(=O)C)O)C)F
• Canonical SMILES: CC(=O)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/C24H30F2O6/c1-12-7-15-16-9-18(25)17-8-14(28)5-6-21(17,3)23(16,26)19(29)10-22(15,4)24(12,31)20(30)11-32-13(2)27/h5-6,8,12,15-16,18-19,29,31H,7,9-11H2,1-4H3/t12-,15-,16-,18-,19-,21-,22-,23-,24-/m0/s1
• InChIKey: ISSQQUKLQJHHOR-RYRQIHONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-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-[(1R,2S,8S,10S,11S,13S,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-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-(acetyloxy)-6,9-difluoro-11,17-dihydroxy-16-methyl-, (6α,11β, 16β)-Pregna-1,4-diene-3,20-dione,; Acetyloxy Diflorasone

Database IDs

• CAS Number: 3826-17-3
• PubChem SID: 162253533
• PubChem CID: 11282395

CALCULATED PROPERTIES

• Acid pKa: 12.43502
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7829758
• LogD (pH = 7.4): 1.7829717
• Log P: 1.7829758
• Molar Refractivity: 111.4678 cm^3
• Polarizability: 43.257286 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Soiid
• Melting Point: 188-190°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A187340

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

REFERENCES

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