gold(1+) ion [(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]sulfanide triethylphosphane

• ChemBase ID: 160903
• Molecular Formular: C20H34AuO9PS
• Molecular Mass: 678.483871
• Monoisotopic Mass: 678.1326833
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)[S-])OC(=O)C)OC(=O)C)OC(=O)C.[Au+].P(CC)(CC)CC
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@@H]([S-])[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C.CCP(CC)CC.[Au+]
• InChI: InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1
• InChIKey: AUJRCFUBUPVWSZ-XTZHGVARSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: gold(1+) ion [(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]sulfanide triethylphosphane
• IUPAC Traditional name: gold(1+) ion [(2S,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]sulfanide triethylphosphine
• Synonyms: [1-(Thio-κS)-β-D-glucopyranose 2,3,4,6-tetraacetato](triethylphosphine)gold; Auranofin

Database IDs

• CAS Number: 34031-32-8
• PubChem SID: 162255038
• PubChem CID: 16667669

CALCULATED PROPERTIES

• Acid pKa: 8.634691
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.20122454
• LogD (pH = 7.4): -0.2237017
• Log P: -0.20092908
• Molar Refractivity: 79.492 cm^3
• Polarizability: 33.07737 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A794750

Auranofin is a new oral gold-based antiarthritis drug. Auranofin inhibits various leukocyte activation pathways at multiple sites. Auranofin inhibits the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. Aurano

REFERENCES

• Kizu, R., et al.: Chem. Pharm. Bull., 41, 1261 (1993)
• Itokazu, M., et al.: Clin. Ther., 17, 60 (1993)
• Kean, W.F., et al.: Br. J. Rheumatol., 36, 560 (1993)