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

• ChemBase编号: 154547
• 分子式: C20H34AuO9PS
• 平均质量: 678.483871
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(triethyl-λ^5-phosphanylidene)aurio]sulfanyl}oxan-2-yl]methyl acetate
• IUPAC传统名: triethylphosphine gold
• 别名: 1-Thio-β-D-glucopyranosatotriethylphosphine gold-2,3,4,6-tetraacetate; 3,4,5-Triacetyloxy-6-(acetyloxymethyl) oxane-2-thiolate triethylphosphanium; SKF 39162; Auranofin

登记号

• EC号: 251-801-9
• MDL号: MFCD00080759

理论计算性质

• 质子受体: 5
• 质子供体: 0
• LogD (pH = 5.5): -1.0203
• LogD (pH = 7.4): -1.0203
• Log P: -1.0203
• 摩尔折射率: 114.885 cm^3
• 极化性: 54.109283 Å^3
• 极化表面积: 114.43 Å^2
• 可自由旋转的化学键: 14
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: DMSO: ≥5 mg/mL
• 外观: powder

安全信息

• RTECS编号: MD6500000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 联合国危险货物编号: 2811
• 德国WGK号: 3
• 联合国危险货物等级: 6.1
• 联合国危险货物包装类别(PG): 3
• 危险公开号: 63-22
• 安全公开号: 36/37
• GHS危险品标识: GHS06; GHS08
• GHS警示词: Danger
• GHS危险声明: H301-H361
• GHS警示性声明: P281-P301 + P310
• 个人保护装置: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• 保存温度: room temp

产品相关信息

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

详细说明

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.