(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-diene-14-carbothioic S-acid

• ChemBase ID: 167410
• Molecular Formular: C21H26F2O4S
• Molecular Mass: 412.4905464
• Monoisotopic Mass: 412.15198675
• SMILES: C1=CC(=O)C=C2[C@]1([C@@]1([C@@H](C[C@@H]2F)[C@H]2[C@](C[C@@H]1O)([C@]([C@@H](C2)C)(C(=O)S)O)C)F)C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(F)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)S)C)C)C
• InChI: InChI=1S/C21H26F2O4S/c1-10-6-12-13-8-15(22)14-7-11(24)4-5-18(14,2)20(13,23)16(25)9-19(12,3)21(10,27)17(26)28/h4-5,7,10,12-13,15-16,25,27H,6,8-9H2,1-3H3,(H,26,28)/t10-,12+,13+,15+,16+,18+,19+,20+,21+/m1/s1
• InChIKey: GLAJUXBOZSWZMM-IDIDPBNYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carbothioic S-acid
• IUPAC Traditional name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-diene-14-carbothioic S-acid
• Synonyms: (6α,11β,16α,17α)-6,9-Difluoro-11,17-dihydroxy-16-methyl-3-oxo-androsta-1,4-diene-17-carbothioic Acid; 6α,9α-Difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17α-carbothioic Acid; 6α,9α-Difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17a-carbothioic Acid

Database IDs

• CAS Number: 80473-92-3
• PubChem SID: 162261543
• PubChem CID: 10024665

CALCULATED PROPERTIES

• Acid pKa: 0.39105546
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.2000489
• LogD (pH = 7.4): 1.2000053
• Log P: 2.3429873
• Molar Refractivity: 103.4768 cm^3
• Polarizability: 40.003155 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White solid
• Melting Point: 222-224°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D445755

An intermediate in the synthesis of fluticasone propionate

REFERENCES

• Meltzer, E.O., et al.: J. Allergy Clin. Immunol., 86, 221 (1990)
• Mitchison, H.C., et al. : Gut, 32 260 (1990)
• Phillipps, G.H., et al.: J. Med. Chem., 37, 3717 (1994)