({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl}oxy)phosphonic acid

• ChemBase编号: 132912
• 分子式: C94H178N2O25P2
• 平均质量: 1798.365042
• 单一同位素质量: 1797.21939247
• SMILES: CCCCCCCCCCCCCC(=O)OC(CCCCCCCCCCC)CC(=O)OC1C(C(OC(C1OP(=O)(O)O)CO)OCC1C(C(C(C(O1)OP(=O)(O)O)NC(=O)CC(CCCCCCCCCCC)O)OC(=O)CC(CCCCCCCCCCC)O)O)NC(=O)CC(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCC(=O)OC(CC(=O)OC1C(NC(=O)CC(OC(=O)CCCCCCCCCCC)CCCCCCCCCCC)C(OCC2OC(OP(=O)(O)O)C(C(C2O)OC(=O)CC(CCCCCCCCCCC)O)NC(=O)CC(CCCCCCCCCCC)O)OC(C1OP(=O)(O)O)CO)CCCCCCCCCCC
• InChI: InChI=1S/C94H178N2O25P2/c1-7-13-19-25-31-37-38-44-50-56-62-68-84(103)115-78(66-60-54-48-42-35-29-23-17-11-5)72-86(105)119-92-88(96-82(101)71-77(65-59-53-47-41-34-28-22-16-10-4)114-83(102)67-61-55-49-43-36-30-24-18-12-6)93(116-79(73-97)90(92)120-122(107,108)109)113-74-80-89(106)91(118-85(104)70-76(99)64-58-52-46-40-33-27-21-15-9-3)87(94(117-80)121-123(110,111)112)95-81(100)69-75(98)63-57-51-45-39-32-26-20-14-8-2/h75-80,87-94,97-99,106H,7-74H2,1-6H3,(H,95,100)(H,96,101)(H2,107,108,109)(H2,110,111,112)
• InChIKey: GZQKNULLWNGMCW-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: ({5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl}oxy)phosphonic acid
• IUPAC传统名: {5-[3-(dodecanoyloxy)tetradecanamido]-6-{[3-hydroxy-5-(3-hydroxytetradecanamido)-4-[(3-hydroxytetradecanoyl)oxy]-6-(phosphonooxy)oxan-2-yl]methoxy}-2-(hydroxymethyl)-4-{[3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-3-yl}oxyphosphonic acid
• 别名: Lipid A, diphosphoryl from Salmonella enterica serotype minnesota Re 595 (Re mutant); Lipid A, diphosphoryl from Escherichia coli F583 (Rd mutant)

登记号

• CAS号: 95991-05-2
• MDL号: MFCD00131510
• PubChem SID: 24896402; 162227189; 24896265
• PubChem CID: 5043498

理论计算性质

• Acid pKa: 0.6083911
• 质子受体: 19
• 质子供体: 10
• LogD (pH = 5.5): 18.968218
• LogD (pH = 7.4): 16.488445
• Log P: 23.97029
• 摩尔折射率: 477.1785 cm^3
• 极化性: 192.28253 Å^3
• 极化表面积: 405.53 Å^2
• 可自由旋转的化学键: 88
• 里宾斯基五规则: false

分子性质

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• 保存温度: 2-8°C

详细说明

Sigma Aldrich - L5399

Biochem/physiol Actions
Lipid A molecules compose the lipid membrane anchoring core components of endotoxins produced by Gram-negative bacteria. Lipid A molecules induce immune responses. Structually, lipid A molecules are composed of two glucosamine unites with varied, species dependent, fatty acyl chain number and identity and degree of phosphorylation. Lipid A, diphosphoryl from Escherichia coli F583 may be used in comparative assessment of the antigenicity of specific structures within different LPA molecules and analogues.