(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6-bis(13C)methyl-9,13-dimethyl(6-13C)-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

• ChemBase ID: 169038
• Molecular Formular: C24H30F2O6
• Molecular Mass: 455.46617091
• Monoisotopic Mass: 455.21110963
• 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]1[C@]2(O[13C](O1)([13CH3])[13CH3])C(=O)CO)C)O)F)F)C
• Canonical SMILES: OCC(=O)[C@@]12O[13C](O[C@@H]1C[C@@H]1[C@]2(C)C[C@H](O)[C@]2([C@H]1C[C@@H](C1=CC(=O)C=C[C@]21C)F)F)([13CH3])[13CH3]
• InChI: InChI=1S/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1/i1+1,2+1,20+1
• InChIKey: FEBLZLNTKCEFIT-BQVDRZGJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6-bis(^1^3C)methyl-9,13-dimethyl(6-^1^3C)-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• IUPAC Traditional name: (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6-bis(^1^3C)methyl-9,13-dimethyl(6-^1^3C)-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• Synonyms: (6α,11β,16α)-6,9-Difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione-13C3; 6α-Fluorotriamcinolone Acetonide-13C3; Fluonid-13C3; Fluzon-13C3; Radiocin-13C3; Synandone-13C3; NSC 92339-13C3; Fluocinolone Acetonide-13C3

Database IDs

• PubChem SID: 162263170
• PubChem CID: 71316785

CALCULATED PROPERTIES

• Acid pKa: 13.351801
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.6043986
• LogD (pH = 7.4): 1.6043981
• Log P: 1.6043986
• Molar Refractivity: 111.4132 cm^3
• Polarizability: 43.155457 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Crystalline Solid
• Melting Point: 265-266°C

DETAILS

Toronto Research Chemicals - F455802

Labelled glucocorticoid; anti-inflammatory.

REFERENCES

• Sammul, et al.: J. Assoc. Off. Agric. Chem., 47, 952 (1964)
• Emerson, M.V., et al.: BioDrugs, 21, 245 (1964)