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Nanchangmycin (Nanchangmycin A) is a polyether antibiotic isolated from Streptomyces nanchangensis NS3226 with similar structure to dianemycin. It is very active against a broad spectrum of harmful nematodes and insects but not for mammals and plants. Nanchangmycin inhibits gram-positive bacteria and can be used as a growth promotant in poultry and to cure coccidiosis in chickens.
Physicochemical Properties
| Molecular Formula | C48H80O13 | |
| Molecular Weight | 889.1 | |
| Exact Mass | 888.521 | |
| Elemental Analysis | C, 63.49; H, 8.73; Na, 2.59; O, 25.19 | |
| CAS # | 65101-87-3 | |
| Related CAS # | Dianemycin;35865-33-9 | |
| PubChem CID | 86278937 | |
| Appearance | White to off-white solid powder | |
| LogP | 6.149 | |
| Hydrogen Bond Donor Count | 3 | |
| Hydrogen Bond Acceptor Count | 14 | |
| Rotatable Bond Count | 13 | |
| Heavy Atom Count | 62 | |
| Complexity | 1580 | |
| Defined Atom Stereocenter Count | 21 | |
| SMILES | C[C@H]1[C@@]2(O[C@]([C@@]3([H])O[C@](O)([C@H](C)C[C@@H]3C)CO)([H])C[C@@H]2C)O[C@]([C@]4(O[C@]5(O[C@]([C@H](C)[C@@H](O)C5)([H])[C@@H](C)/C=C(C)/C([C@H](C)C[C@H](C)C([O-])=O)=O)CC4)C)([H])C[C@@H]1O[C@@]6([H])O[C@@H]([C@@H](OC)CC6)C.[Na+] |
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| InChi Key | XMAIRYYXDCNFKP-DYTQFKGPSA-M | |
| InChi Code | InChI=1S/C47H78O14.Na/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);/q;+1/p-1/b24-17+;/t25-,26+,27+,28+,29-,30+,31-,32-,33-,34+,35+,36+,37-,38-,39?,41-,42+,44+,45-,46+,47+;/m1./s1 | |
| Chemical Name | Sodium (E,2S,4R,8S)-8-[(2S,5R,7S,8R,9R)-7-hydroxy-2-[(2R,4S,5S,7R,9S,10R)-2-[(2S,3S,5R,6R)-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-9-[(5S,6R)-5-methoxy-6-methyloxan-2-yl]oxy-4,10-dimethyl-1,6-dioxaspiro[4.5]decan-7-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2,4,6-trimethyl-5-oxonon-6-enoate | |
| Synonyms |
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| HS Tariff Code | 2934.99.9001 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets |
Bacteria Zika virus |
| ln Vitro | Nanchangmycin can be used to treat chicken coccidiosis and as a growth promoter in poultry. Nanchangmycin is effective against malaria strains that are resistant to drugs[1]. Zika virus (ZIKV) entry was effectively inhibited by nanchangmycin in all tested cell types, including primary cells that are physiologically relevant. All three ZIKV strains are significantly less likely to infect any of the three cell types when nanchangmycin is used. Nanchangmycin exhibits low toxicity within the range of 0.1 to 0.4 μM, where the IC50s for infection fall within this range. Furthermore, nanchangmycin inhibits DENV in a variety of cell types[2]. |
| References |
[1]. Mechanism of thioesterase-catalyzed chain release in the biosynthesis of the polyether antibiotic nanchangmycin. Chem Biol. 2008 May;15(5):449-58. [2]. Screening Bioactives Reveals Nanchangmycin as a Broad Spectrum Antiviral Active against Zika Virus. Cell Rep. 2017 Jan 17;18(3):804-815. |
Solubility Data
| Solubility (In Vitro) |
DMSO : ~100 mg/mL ( ~112.47 mM ) Ethanol : ~100 mg/mL |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.08 mg/mL (2.34 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.08 mg/mL (2.34 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.08 mg/mL (2.34 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 4: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: 2.08 mg/mL (2.34 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1247 mL | 5.6237 mL | 11.2473 mL | |
| 5 mM | 0.2249 mL | 1.1247 mL | 2.2495 mL | |
| 10 mM | 0.1125 mL | 0.5624 mL | 1.1247 mL |