(1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(6,8,8-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 171798
• Molecular Formular: C21H27FO5
• Molecular Mass: 378.4344832
• Monoisotopic Mass: 378.18425218
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1CC[C@]2(O)C(=O)CO)C)O)F)C
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C21H27FO5/c1-18-7-5-13(24)9-12(18)3-4-15-14-6-8-20(27,17(26)11-23)19(14,2)10-16(25)21(15,18)22/h5,7,9,14-16,23,25,27H,3-4,6,8,10-11H2,1-2H3/t14-,15-,16-,18-,19-,20-,21-/m0/s1
• InChIKey: WAIJIHDWAKJCBX-BULBTXNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,2S,10S,11S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (11β)-9-Fluoro-11,17,21-trihydroxypregna-1,4-diene-3,20-dione-d3; 9-Fluoro-11β,17,21-trihydroxy-pregna-1,4-diene-3,20-dione-d3; 9-Fluoroprednisolone-d3; 9α-Fluoro-1-cortisol-d3; Δ-Fluorocortisone-d3; NSC 12174-d3; Isoflupredone-d3 (Major)

Database IDs

• PubChem SID: 164227708
• PubChem CID: 71749560

CALCULATED PROPERTIES

• Acid pKa: 12.549859
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.3165969
• LogD (pH = 7.4): 1.3165938
• Log P: 1.3165969
• Molar Refractivity: 98.0213 cm^3
• Polarizability: 37.78934 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Off-White Solid
• Melting Point: 241-243°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - I816602

Labelled Isoflupredone (I816600). Anti-inflammatory.

REFERENCES

• Buchwald, P., et al.: Steroids, 73, 193 (2008)
• Holbeck, S., et al.: Mol. Endocrinol., 24, 1287 (2008)