sodium (1R,2S,4R,5R,8R,9S,11R)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.02,11.04,8]tridec-12-ene-1-carboxylate

• ChemBase编号: 153926
• 分子式: C27H39NaO8
• 平均质量: 514.58353
• 单一同位素质量: 514.25426249
• SMILES: C[C@@H]1CC[C@@H]2[C@@H]1C[C@@]1([C@@H]3C[C@]2([C@]1(C(=C3)C(C)C)C(=O)[O-])C=O)CO[C@H]1[C@H]([C@@H]([C@@H]([C@H](O1)C)OC)O)O.[Na+]
• Canonical SMILES: CO[C@@H]1[C@@H](C)O[C@H]([C@H]([C@@H]1O)O)OC[C@@]12C[C@@H]3[C@H](C)CC[C@H]3[C@@]3([C@@]2(C(=O)[O-])C(=C[C@H]1C3)C(C)C)C=O.[Na+]
• InChI: InChI=1S/C27H40O8.Na/c1-13(2)19-8-16-9-25(11-28)18-7-6-14(3)17(18)10-26(16,27(19,25)24(31)32)12-34-23-21(30)20(29)22(33-5)15(4)35-23;/h8,11,13-18,20-23,29-30H,6-7,9-10,12H2,1-5H3,(H,31,32);/q;+1/p-1/t14-,15-,16+,17-,18-,20+,21+,22-,23-,25+,26+,27+;/m1./s1
• InChIKey: ILUKWKGTAAZHDW-IGICPMPSSA-M

名称和登记号

名称

• IUPAC标准名: sodium (1R,2S,4R,5R,8R,9S,11R)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-5-methyl-13-(propan-2-yl)tetracyclo[7.4.0.0^2,^1^1.0^4,^8]tridec-12-ene-1-carboxylate
• IUPAC传统名: sodium (1R,2S,4R,5R,8R,9S,11R)-2-({[(2R,3S,4S,5S,6R)-3,4-dihydroxy-5-methoxy-6-methyloxan-2-yl]oxy}methyl)-9-formyl-13-isopropyl-5-methyltetracyclo[7.4.0.0^2,^1^1.0^4,^8]tridec-12-ene-1-carboxylate
• 别名: Sordarin sodium salt 钠盐; Sordarin sodium salt

登记号

• CAS号: 463356-00-5
• MDL号: MFCD08277029
• PubChem SID: 24899480; 162248065
• PubChem CID: 23702146

理论计算性质

• Acid pKa: 4.179116
• 质子受体: 8
• 质子供体: 2
• LogD (pH = 5.5): 0.7678338
• LogD (pH = 7.4): -0.941259
• Log P: 2.106304
• 摩尔折射率: 137.3557 cm^3
• 极化性: 50.448715 Å^3
• 极化表面积: 125.35 Å^2
• 可自由旋转的化学键: 7
• 里宾斯基五规则: false

分子性质

理化性质

• 溶解度: H2O: soluble ≤10 mg/mL
• 外观: solid

安全信息

• 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: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 生物来源: from Sordaria araneosa
• 运输包装: wet ice
• Empirical Formula (Hill Notation): C27H39NaO8

详细说明

Sigma Aldrich - S1442

Biochem/physiol Actions
Sordarin is an antifungal metabolite possessing a tetracyclic diterpene glycoside structure. It is a highly potent inhibitor of eukaryotic protein synthesis with selectivity for the fungal translation machinery. The elongation factor EF-2 is the molecular target for sordarin. It blocks ribosomal translocation by stabilizing the EF2-ribosome complex in a manner similar to that of fusidic acid in the bacterial system. Additional cellular components (including rpP0, which is an essential protein of the ribosomal large subunit stalk) are involved in its mechanism of action. Sordarin inhibits in vitro translation in the pathogenic fungi C. albicans, C. glabrata, and C. neoformans. In addition to its therapeutic potential, sordarin is a useful tool for the analysis of protein translation events.