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

• ChemBase ID: 167589
• Molecular Formular: C22H31FO5
• Molecular Mass: 394.4769432
• Monoisotopic Mass: 394.21555231
• SMILES: C1CC(=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)CC[C@]12C)F
• InChI: InChI=1S/C22H31FO5/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/h9,12,15-17,24,26,28H,4-8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
• InChIKey: YYZXYYHUGHQGHI-CXSFZGCWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13R,14R,15S,17S)-1-fluoro-14,17-dihydroxy-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,14R,15S,17S)-1-fluoro-14,17-dihydroxy-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-11,17,21-trihydroxy-16-methylpregn-4-ene-3,20-dione; 9-Fluoro-11β,17,21-trihydroxy-16α-methylpregn-4-ene-3,20-dione; RU 25008; 1,2-Dihydro Dexamethasone

Database IDs

• CAS Number: 426-17-5
• PubChem SID: 162261722
• PubChem CID: 22792547

CALCULATED PROPERTIES

• Acid pKa: 12.424369
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.6837461
• LogD (pH = 7.4): 1.683742
• Log P: 1.6837462
• Molar Refractivity: 101.3996 cm^3
• Polarizability: 39.866886 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D449010

A derivatives of Dexamethasone (D298800), an analog of cortical hormones.

REFERENCES

• Giesen, E.M., et al.: Molec. Cell. Endocrinol., 22, 153 (1981)