2-[(1S,2S,4R,8S,9S,11S,12R,13S,19R)-12-fluoro-11,19-dihydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-8-yl]-2-oxoethyl acetate

• ChemBase ID: 170080
• Molecular Formular: C26H33FO8
• Molecular Mass: 492.5338232
• Monoisotopic Mass: 492.21594624
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](C[C@H]2O)[C@H]2[C@](C[C@@H]1O)([C@]1([C@@H](C2)OC(O1)(C)C)C(=O)COC(=O)C)C)F)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]12OC(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)O)F)(C)C
• InChI: InChI=1S/C26H33FO8/c1-13(28)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(30)17-8-14(29)6-7-23(17,4)25(16,27)19(31)11-24(15,26)5/h6-8,15-16,18-19,21,30-31H,9-12H2,1-5H3/t15-,16-,18+,19-,21+,23-,24-,25-,26+/m0/s1
• InChIKey: JDZIWTDCPALRKC-CCGQCGMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19R)-12-fluoro-11,19-dihydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl acetate
• IUPAC Traditional name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S,19R)-12-fluoro-11,19-dihydroxy-6,6,9,13-tetramethyl-16-oxo-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-8-yl]-2-oxoethyl acetate
• Synonyms: (6α,11β,16α)-21-(Acetyloxy)-9-fluoro-6,11-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-pregna-1,4-diene-3,20-dione; 6β-Hydroxy 21-(Acetyloxy) Triamcinolone Acetonide

Database IDs

• CAS Number: 72559-83-2
• PubChem SID: 164225990
• PubChem CID: 22810918

CALCULATED PROPERTIES

• Acid pKa: 13.581156
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 1.1544322
• LogD (pH = 7.4): 1.1544319
• Log P: 1.1544322
• Molar Refractivity: 122.2568 cm^3
• Polarizability: 47.89291 Å^3
• Polar Surface Area: 119.36 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Brown Solid

DETAILS

Toronto Research Chemicals - H750010

Derivative of Triamcinolone Acetonide, a glucocorticoid, antiasthmatic (inhalant); antiallergic (nasal).

REFERENCES

• Florey, K., et al.: Anal. Profiles Drug Subs., 1, 397 (1972)
• Bernstein, I.L., et al.: Chest, 81, 20 (1972)