(1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(2H2)acetyl]-2,13,15-trimethyl(6,8,8-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 166716
• Molecular Formular: C22H29FO5
• Molecular Mass: 392.4610632
• Monoisotopic Mass: 392.19990225
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)C)(C(=O)CO)O)C)F)C
• 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]2CCC2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
• InChIKey: UREBDLICKHMUKA-CXSFZGCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,13,15-trimethyl(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,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,13,15-trimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: Decacort-d5; Decaderm-d5; Decadron-d5; Decalix-d5; Decasone-d5; Dekacort-d5; Dexamethasone-d5; (11β,16α)-9-Fluoro-11,17,21-trihydroxy-16-pregna-1,4-diene-3,20-dione-d5; 16α-Methyl-9α-fluoroprednisolone-d5; Aeroseb-Dex-d5; Corson-d5; Cortisumman-d5

Database IDs

• CAS Number: 358731-91-6
• PubChem SID: 162260849
• PubChem CID: 71315850

CALCULATED PROPERTIES

• Acid pKa: 12.423736
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6815696
• LogD (pH = 7.4): 1.6815655
• Log P: 1.6815697
• Molar Refractivity: 102.4929 cm^3
• Polarizability: 39.61867 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 230-232°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D298802

A glucocorticoid anti-inflammatory agent. Regulates T cell survival, growth, and differentiation. Inhibits the induction of nitric oxide synthase.

REFERENCES

• Wershil, B.K., et al.: Int. Arch. Allergy Immunol., 107, 323 (1995)
• Riccardi, C., et al.: Cell Death Diff., 6, 1182 (1995)
• Llanos, S.L. and Roldan, A.: Bio Cell, 23, 29 (1999)