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 ID: 153926
• Molecular Formular: C27H39NaO8
• Molecular Mass: 514.58353
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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 Traditional name: 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
• Synonyms: Sordarin sodium salt; Sordarin sodium salt 钠盐

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 4.179116
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.7678338
• LogD (pH = 7.4): -0.941259
• Log P: 2.106304
• Molar Refractivity: 137.3557 cm^3
• Polarizability: 50.448715 Å^3
• Polar Surface Area: 125.35 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble ≤10 mg/mL
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Biological Source: from Sordaria araneosa
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C27H39NaO8

DETAILS

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.