SML2251

Nanchangmycin

≥98% (HPLC)

• Synonym(s): (2S,4R,6E,8S)-8-[(2S,2′R,4′S,5R,5′S,7R,7′R,8R,9S,9′S,10′R)-9-hydroxy-2,4′,8,10′-tetramethyl-2′-[(2S,3S,5R,6R)-tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl]-9′-[[(2S,5S,6R)-tetrahydro-5-methoxy-6-methyl-2H-pyran-2-yl]oxy][2,7′-bi-1,6-dioxaspiro[4.5]dec]-7-yl]-2,4,6-trimethyl-5-oxo-6-nonenoic acid
• Empirical Formula (Hill Notation): C₄₇H₇₈O₁₄
• CAS Number: 35865-33-9
• Molecular Weight: 867.11
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• biological source: Streptomyces nanchangensis
• assay: ≥98% (HPLC)
• form: powder
• color: white to beige
• solubility: DMSO: 2 mg/mL, clear
• storage temp.: −20°C
• SMILES string: OC([C@@H](C)C[C@@H](C)C(/C(C)=C/[C@H](C)[C@]1([H])[C@H](C)[C@@H](O)C[C@]2(CC[C@]([C@@]3([H])C[C@H](O[C@@]4([H])O[C@H](C)[C@@H](OC)CC4)[C@@H](C)[C@@]5(O[C@]([C@@]6([H])O[C@@](O)(CO)[C@H](C)C[C@@H]6C)([H])C[C@@H]5C)O3)(C)O2)O1)=O)=O
• InChI: 1S/C47H78O14/c1-24(40(50)25(2)18-28(5)43(51)52)17-26(3)41-31(8)34(49)22-45(59-41)16-15-44(11,61-45)38-21-36(56-39-14-13-35(54-12)33(10)55-39)32(9)47(58-38)30(7)20-37(57-47)42-27(4)19-29(6)46(53,23-48)60-42/h17,25-39,41-42,48-49,53H,13-16,18-23H2,1-12H3,(H,51,52)/b24-17+
• InChI key: FELYAZAWTURXNF-JJIBRWJFSA-N

Description

Biochem/physiol Actions

Nanchangmycin is a broad spectrum polyether antibiotic recently shown to inhibit Zika virus entry. Nanchangmycin was found to potently inhibit entry in three distinct cell types including human brain microvascular endothelial cells (HBMECs) with two different strains of Zika virus. It was also found effective against other viruses such as West Nile, dengue, and chikungunya.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• Storage Class: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable