(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]icosa-14,17,19-trien-16-one

• ChemBase ID: 165705
• Molecular Formular: C24H29FO6
• Molecular Mass: 432.4818632
• Monoisotopic Mass: 432.19481687
• SMILES: C1=C[C@]2(C(=CC1=O)C=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)CO)C)O)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]1C=CC1=CC(=O)C=C[C@]21C)F)(C)C
• InChI: InChI=1S/C24H29FO6/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/h5-9,15-17,19,26,28H,10-12H2,1-4H3/t15-,16-,17-,19+,21-,22-,23-,24+/m0/s1
• InChIKey: JWPZLQJLMNKVAZ-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]icosa-14,17,19-trien-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]icosa-14,17,19-trien-16-one
• Synonyms: 9-Fluoro-(11β,16α),17,21-tetrahydroxypregna-1,4,6-triene-3,20-dione Cyclic 16,17-Acetal With Acetone; 6,7-Dehydro Triamcinolone Acetonide

Database IDs

• CAS Number: 1893-84-1
• PubChem SID: 162259838
• PubChem CID: 29976836

CALCULATED PROPERTIES

• Acid pKa: 13.395565
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.5821962
• LogD (pH = 7.4): 1.5821958
• Log P: 1.5821962
• Molar Refractivity: 112.7064 cm^3
• Polarizability: 43.118694 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D230565

A derivative of Triamcinolone acetonide. A corticosteroid.

REFERENCES

• Sulzberger, M., et al.: J. Invest. Dermatol., 19, 101 (1952)
• Diassi, P.A., et al.: J. Med. Chem., 10, 551 (1952)