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-oxoacetic acid

• ChemBase ID: 171394
• Molecular Formular: C24H29FO8
• Molecular Mass: 464.4806632
• Monoisotopic Mass: 464.18464611
• 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(OC(O1)(C)C)C(=O)C(=O)O)C)O)F)O)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@H](O)C[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/C24H29FO8/c1-20(2)32-17-9-12-13-8-15(27)14-7-11(26)5-6-21(14,3)23(13,25)16(28)10-22(12,4)24(17,33-20)18(29)19(30)31/h5-7,12-13,15-17,27-28H,8-10H2,1-4H3,(H,30,31)/t12-,13-,15+,16-,17+,21-,22-,23-,24-/m0/s1
• InChIKey: CBSSHJZTNNYCED-ZKNYGLMYSA-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-oxoacetic acid
• IUPAC Traditional name: [(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](oxo)acetic acid
• Synonyms: (6β,11β,16α)-9-Fluoro-6,11-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-3,20-dioxopregna-1,4-dien-21-oic Acid; 6β-Hydroxy-21-oic Triamcinolone Acetonide

Database IDs

• CAS Number: 68263-02-5
• PubChem SID: 164227304
• PubChem CID: 29982178

CALCULATED PROPERTIES

• Acid pKa: 3.410711
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.587179
• LogD (pH = 7.4): -1.9100347
• Log P: 1.490149
• Molar Refractivity: 113.198 cm^3
• Polarizability: 44.00943 Å^3
• Polar Surface Area: 130.36 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H970045

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)