(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-[(3,3,3-2H3)propanoyloxy]tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carboxylic acid

• ChemBase ID: 169300
• Molecular Formular: C24H30F2O6
• Molecular Mass: 452.4882064
• Monoisotopic Mass: 452.20104512
• SMILES: C1=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@]2(OC(=O)CC)C(=O)O)C)C)O)F)F)C
• Canonical SMILES: CCC(=O)O[C@]1(C(=O)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/c1-5-19(29)32-24(20(30)31)12(2)8-14-15-10-17(25)16-9-13(27)6-7-21(16,3)23(15,26)18(28)11-22(14,24)4/h6-7,9,12,14-15,17-18,28H,5,8,10-11H2,1-4H3,(H,30,31)/t12-,14+,15+,17+,18+,21+,22+,23+,24+/m1/s1
• InChIKey: DEDYNJVITFVPOG-CQRCZTONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-[(3,3,3-^2H₃)propanoyloxy]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylic acid
• IUPAC Traditional name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-[(3,3,3-^2H₃)propanoyloxy]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carboxylic acid
• Synonyms: 6α,11β,16α,17α)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy-d3)-androsta-1,4-diene-17-carboxylic Acid; Fluticasone 17β-Carboxylic Acid Propionate-d3

Database IDs

• PubChem SID: 162263432
• PubChem CID: 71316900

CALCULATED PROPERTIES

• Acid pKa: 4.3540287
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.7969813
• LogD (pH = 7.4): 0.04812574
• Log P: 2.9711342
• Molar Refractivity: 110.8414 cm^3
• Polarizability: 43.087635 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 208-211°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F599497

Labelled Fluticasone 17β-Carboxylic Acid Propionate (F599495). An impurity formed in the synthesis of Fluticasone propionate (F599500).

REFERENCES

• Phillips, G., et al.: J. Med. Chem., 37, 3717 (1994)