[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-λ5-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate

• ChemBase ID: 154547
• Molecular Formular: C20H34AuO9PS
• Molecular Mass: 678.483871
• Monoisotopic Mass: 678.1326833
• SMILES: CCP(=[Au]S[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)(CC)CC
• Canonical SMILES: CCP(=[Au]S[C@@H]1O[C@H](COC(=O)C)[C@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)(CC)CC
• 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: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-λ^5-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate
• IUPAC Traditional name: triethylphosphine gold
• Synonyms: 1-Thio-β-D-glucopyranosatotriethylphosphine gold-2,3,4,6-tetraacetate; 3,4,5-Triacetyloxy-6-(acetyloxymethyl) oxane-2-thiolate triethylphosphanium; SKF 39162; Auranofin

Database IDs

• EC Number: 251-801-9
• MDL Number: MFCD00080759

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -1.0203
• LogD (pH = 7.4): -1.0203
• Log P: -1.0203
• Molar Refractivity: 114.885 cm^3
• Polarizability: 54.109283 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: ≥5 mg/mL
• Apperance: powder

Safety Information

• RTECS: MD6500000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 63-22
• Safety Statements: 36/37
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H361
• GHS Precautionary statements: P281-P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C20H34AuO9PS

DETAILS

Sigma Aldrich - A6733

Application
Auranofin inhibits both leukocyte activation pathways at multiple sites and the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. Auranofin also inhibits 5-lipoxygenase in human neutrophils, IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5 and selenoenzyme thioredoxin reductase (TrxR) which is involved in the defense against oxidative stress. Auranofin is a disease-modifying antirheumatic drug (DMARD) and has been used to study the anti-proliferative effects against OVCAR-3 human ovarian carcinoma cells.
Biochem/physiol Actions
Auranofin inhibits various leukocyte activation pathways at multiple sites. Auranofin inhibits the release of inflammatory mediators from human macrophages, basophils, and pulmonary mast cells. The compound also inhibits 5-lipoxygenase in human neutrophils. Auranofin is a disease-modifying antirheumatic drug (DMARD). The compound is a potent inhibitor of selenoenzyme thioredoxin reductase (TrxR), which is involved in defense against oxidative stress. Auranofin is an efficient inducer of mitochondrial membrane permeability transition pore in the presence of calcium ions related to its inhibition of mitochondrial thioredoxin reductase. Auranofin inhibits IKB kinase (IKK) by modifying Cys-179 of the IKKβ subunit 5.