(1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadec-6-en-5-one

• ChemBase ID: 167562
• Molecular Formular: C22H31FO4
• Molecular Mass: 378.4775432
• Monoisotopic Mass: 378.22063769
• SMILES: C1C(=O)C=C2[C@](C1)([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@H]([C@@H](C2)C)C(=O)CO)C)F)C
• Canonical SMILES: OCC(=O)[C@H]1[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)CC[C@]12C)F
• InChI: InChI=1S/C22H31FO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-21(13,3)22(15,23)18(27)10-20(16,2)19(12)17(26)11-24/h9,12,15-16,18-19,24,27H,4-8,10-11H2,1-3H3/t12-,15+,16+,18+,19-,20+,21+,22+/m1/s1
• InChIKey: GROORMIERUNSSM-IIEHVVJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• IUPAC Traditional name: (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one
• Synonyms: (11β,16α)-9-Fluoro-11,21-dihydroxy-16-methylpregn-4-ene-3,20-dione; 9α-Fluoro-11β,21-dihydroxy-16α-methylpregn-4-ene-3,20-dione; 1,2-Dihydro Desoxymetasone

Database IDs

• CAS Number: 432-54-2
• PubChem SID: 162261695
• PubChem CID: 22793410

CALCULATED PROPERTIES

• Acid pKa: 13.446711
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 2.3532176
• LogD (pH = 7.4): 2.3532171
• Log P: 2.3532176
• Molar Refractivity: 100.0766 cm^3
• Polarizability: 39.207657 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White to Pale Pink Solid
• Melting Point: 176-178°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D448875

A metabolite of Desoxymetasone (D296970).

REFERENCES

• Schriks, M., et al.: Environ. Sci. Technol., 44, 4766 (2010)
• Baeck, M., et al.: Eur. J. Dermatol., 20, 102 (2010)
• Lee, P., et al.: Bioorg. Med. Chem. Lett., 20, 69 (2010)