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A 26771B is a sixteen-membered macrolide lactone antibiotic (Berkeleylactones) that was originally isolated from Penicillium turbatum. In recent years, promising synthetic derivatives of macrolactone natural product (-)-A26771B have been designed and synthesized both from semisynthesis and total synthesis. Further optimization led to the first synthesis of macrolactam analogs of (-)-A26771B with improved antibacterial activity and metabolic stability. One of the Berkeleylactones exhibited potent antimicrobial activity with low micromolar activity (MIC = 1-2 μg/mL) against four MRSA strains, as well as Bacillus anthracis, Streptococcus pyogenes, Candida albicans, and Candida glabrata.
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Physicochemical Properties
| Molecular Formula |
C20H30O7
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| Molecular Weight |
382.4480
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| Exact Mass |
382.199
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| CAS # |
56448-20-5
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| Related CAS # |
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| PubChem CID |
11143436
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
3.344
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
7
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
27
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| Complexity |
538
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| Defined Atom Stereocenter Count |
2
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| SMILES |
O1C(C([H])=C([H])C([C@]([H])(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C([H])([H])[H])OC(C([H])([H])C([H])([H])C(=O)O[H])=O)=O)=O |c:3|
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| InChi Key |
CAOCHWFVLJETKN-SADTYBKJSA-N
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| InChi Code |
InChI=1S/C20H30O7/c1-15-9-7-5-3-2-4-6-8-10-17(16(21)11-13-19(24)26-15)27-20(25)14-12-18(22)23/h11,13,15,17H,2-10,12,14H2,1H3,(H,22,23)/b13-11+/t15-,17+/m1/s1
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| Chemical Name |
4-[[(3E,6S,16R)-16-methyl-2,5-dioxo-1-oxacyclohexadec-3-en-6-yl]oxy]-4-oxobutanoic acid
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| Synonyms |
| A 26771B; A-26771B; A26771B |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder-20°C 3 years
4°C 2 years
In solvent -80°C 6 months
-20°C 1 month
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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)
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Biological Activity
| ln Vitro |
In vitro activity:
Kinase Assay:
Cell Assay: |
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| ln Vivo |
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| Animal Protocol |
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| References |
Bioorg Med Chem Lett.2011 Aug 15;21(16):4768-72;J Antibiot (Tokyo).1977 Jul;30(7):571-5;J Nat Prod.2017 Apr 28;80(4):1150-1160.
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Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
(Please use freshly prepared in vivo formulations for optimal results.)
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| Preparing Stock Solutions |
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1 mg |
5 mg |
10 mg |
| 1 mM |
2.6147 mL |
13.0736 mL |
26.1472 mL |
| 5 mM |
0.5229 mL |
2.6147 mL |
5.2294 mL |
| 10 mM |
0.2615 mL |
1.3074 mL |
2.6147 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles. |
