2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-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-oxoacetic acid

• ChemBase ID: 163760
• Molecular Formular: C24H29FO7
• Molecular Mass: 448.4812632
• Monoisotopic Mass: 448.18973149
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]1[C@]2(OC(O1)(C)C)C(=O)C(=O)O)C)O)F)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)CC[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@@H]1[C@]2(OC(O1)(C)C)C(=O)C(=O)O)C)C
• InChI: InChI=1S/C24H29FO7/c1-20(2)31-17-10-15-14-6-5-12-9-13(26)7-8-21(12,3)23(14,25)16(27)11-22(15,4)24(17,32-20)18(28)19(29)30/h7-9,14-17,27H,5-6,10-11H2,1-4H3,(H,29,30)/t14-,15-,16-,17+,21-,22-,23-,24-/m0/s1
• InChIKey: WSNWGUDQZFLDGP-DGGKRYAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-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-oxoacetic acid
• IUPAC Traditional name: [(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-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](oxo)acetic acid
• Synonyms: (11β,16α)-9-Fluoro-11-hydroxy-16,17-[(1-methylethylidene)bis(oxy)]-3,20-dioxopregna-1,4-dien-21-oic Acid; 21-Carboxylic Acid Triamcinolone Acetonide

Database IDs

• CAS Number: 53962-41-7
• PubChem SID: 162257895
• PubChem CID: 22798797

CALCULATED PROPERTIES

• Acid pKa: 3.4766698
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.7068674
• LogD (pH = 7.4): -0.66126275
• Log P: 2.7209601
• Molar Refractivity: 111.6825 cm^3
• Polarizability: 43.329082 Å^3
• Polar Surface Area: 110.13 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C178550

A metabolite of Triamcinolone acetonide.

REFERENCES

• Edsbacker, S., et al.: Drug Metab. Dispos., 11, 590 (1983)
• Szefler, S., et al.: Eur. J. Clin. Pharmacol., 30, 323 (1983)
• Hansel, T., et al.: J. Immunol. Methods, 145, 105 (1983)
• Argenti, D., et al.: J. Clin. Pharmacol., 39, 695 (1983)