(6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid

• ChemBase编号: 126205
• 分子式: C28H38O7
• 平均质量: 486.59712
• 单一同位素质量: 486.26175356
• SMILES: O=C(O)/C(=C/C=C(\C)/[C@H](OC)C/C=C/C=C/CC/C=C/C[C@@H](/C=C/C(=C/C(=O)O)/CC(=O)O)C)/C
• Canonical SMILES: CO[C@@H](/C(=C/C=C(/C(=O)O)\C)/C)C/C=C/C=C/CC/C=C/C[C@@H](/C=C/C(=C/C(=O)O)/CC(=O)O)C
• InChI: InChI=1S/C28H38O7/c1-21(15-18-24(19-26(29)30)20-27(31)32)13-11-9-7-5-6-8-10-12-14-25(35-4)22(2)16-17-23(3)28(33)34/h6,8-12,15-19,21,25H,5,7,13-14,20H2,1-4H3,(H,29,30)(H,31,32)(H,33,34)/t21-,25+/m0/s1
• InChIKey: SHCXABJSXUACKU-SQJMNOBHSA-N

名称和登记号

名称

• IUPAC标准名: (6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
• IUPAC传统名: (6R,17S)-20-(carboxymethyl)-6-methoxy-2,5,17-trimethyldocosa-2,4,8,10,14,18,20-heptaenedioic acid
• 别名: Bongkrekic acid solution; Bongkrekic acid; Bonqkrekik acid; Flavotoxin A; Bongkrek acid

登记号

• CAS号: 11076-19-0
• EC号: 231-791-2
• MDL号: MFCD01729616
• PubChem SID: 24891898; 162220546
• PubChem CID: 25463; 71308165
• Chemspider ID: 4938689
• 医学主题词(MeSH): Bongkrekic+acid
• 维基百科标题: Bongkrek_acid

理论计算性质

• Acid pKa: 4.070981
• 质子受体: 7
• 质子供体: 3
• LogD (pH = 5.5): 2.6914325
• LogD (pH = 7.4): -2.5894036
• Log P: 5.495726
• 摩尔折射率: 144.1274 cm^3
• 极化性: 52.83922 Å^3
• 极化表面积: 121.13 Å^2
• 可自由旋转的化学键: 17
• 里宾斯基五规则: false

分子性质

理化性质

• 熔点: 50-60 °C

安全信息

• 安全公开号: R
• 个人保护装置: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• 保存温度: -20°C

产品相关信息

• 纯度: ≥95% (HPLC)
• 浓度: ~1 mg/mL
• 生物来源: from Pseudomonas cocovenenans
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C28H38O7

详细说明

Sigma Aldrich - B6179

Biochem/physiol Actions
An antiapoptotic agent, it protects against NMDA receptor induced neuronal apoptosis,- extends cell survival in cells undergoing apoptosis following infection with viral vectors and abrogates apoptosis induced by hydrogen peroxide in T-cells. It is an inhibitor of adenine nucleotide translocase, which is a component of the mitochondrial permeability transition (MPT) pore complex. Bongkrekic acid prevents mitochondrial depolarization, swelling, rupture of mitochondrial outer membrane, and release of apoptogenic proteins such as cytochrome c. This phenomenon was observed during staurosporine induced apoptosis in Jurkat cells, in HepG2 undergoing apoptosis following TNF-α and ethanol.
Other Notes
The toxic principle of P. cocovenenans.
Physical form
Solution in 0.01 M Tris buffer, pH 7.5.