(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icos-17-en-16-one

• ChemBase ID: 169139
• Molecular Formular: C24H33FO6
• Molecular Mass: 436.5136232
• Monoisotopic Mass: 436.226117
• SMILES: C1C(=O)C=C2[C@](C1)([C@@]1([C@@H](CC2)[C@H]2[C@](C[C@@H]1O)([C@]1([C@@H](C2)OC(O1)(C)C)C(=O)CO)C)F)C
• Canonical SMILES: OCC(=O)[C@@]12OC(O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1CCC1=CC(=O)CC[C@]21C)F)(C)C
• InChI: InChI=1S/C24H33FO6/c1-20(2)30-19-10-16-15-6-5-13-9-14(27)7-8-21(13,3)23(15,25)17(28)11-22(16,4)24(19,31-20)18(29)12-26/h9,15-17,19,26,28H,5-8,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1
• InChIKey: TZFZVQNBXVBQDC-JNQJZLCISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icos-17-en-16-one
• IUPAC Traditional name: (1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icos-17-en-16-one
• Synonyms: 11β,16α,17α,21-Tetrahydroxy-9α-fluoropregn-4-ene-3,20-dione 16,17-Acetonide; (11β,16α)-9-Fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione; 9-fluoro-11β,16α,17,21-Tetrahydroxypregn-4-ene-3,20-dione cyclic 16,17-Acetal with Acetone; NSC 21915; 9-Fluoro-16α,17-(isopropylidenedioxy) Corticosterone

Database IDs

• CAS Number: 1524-86-3
• PubChem SID: 162263271
• PubChem CID: 228786

CALCULATED PROPERTIES

• Acid pKa: 13.408025
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.9462943
• LogD (pH = 7.4): 1.946294
• Log P: 1.9462944
• Molar Refractivity: 110.4965 cm^3
• Polarizability: 43.61609 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 249-254°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - F592050

Synthetic fluorinated corticosteroid tested for inhibition of granuloma in rats and for vasoconstriction activity in human subjects; potential topical antiinflammatory agent.

REFERENCES

• Hannah, J. et al.: J. Med. Chem., 18, 168 (1975)