A 26771B

Alias: A 26771B; A-26771B; A26771B

Cat No.:V3077 Purity: ≥98%

COA Product Data Instructions for use SDS

A 26771B is a sixteen-membered macrolide lactone antibiotic (Berkeleylactones) that was originally isolated from Penicillium turbatum.

A 26771B Chemical Structure CAS No.: 56448-20-5
Product category: Others 8

This product is for research use only, not for human use. We do not sell to patients.

Size	Price
500mg
1g
Other Sizes

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Major Universities, Research Institutions, Biotech & Pharma
Citations by Top Journals: Nature, Cell, Science, etc.

Top Publications Citing lnvivochem Products

Nature 2021, 597(7874):119-125.

Cell 2020,183:1202-1218.e25.

Science Adv 2022: 8, eabm9427.

Nature 597, 119–125 (2021)

Cell Stem Cell 2020,26(6):845-861.e12.

Science Trans Med 2023,15(701):eadd7872.

STTT 2023,8(1):91.

Cell Reports 2023,42(4):112313

Science Trans Med 2023, 15: eadd7872.

Cancer Cell 2021,39(4):529-547.e7.

Cancer Discov 2022,12(4):1106-1127.

Immunity 2023,56(3):620-634.e11.

J Am Chem Soc 2022,144:21831-21836.

Cell 2020,183:1202-1218.e25.

Science Adv 2022:8,eabm9427.

Nature 2021,597(7874):119-125.

Cell 2020,183:1202-1218.e25.

PNAS Nexus 2022,1(3):pgac063.

ACS Nano 2023,17(10):9110-9125.

Biomaterial 2023 Sep16:302:122333.

Purity & Quality Control Documentation

Current batch：

Purity: ≥98%

COA

MSDS

Instructions

Product Description
Bioactivity & Protocols
Physicochemical Properties
Solubility Data
Calculators
Biological Data

Product Description

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.

Biological Activity I Assay Protocols (From Reference)

ln Vitro

In vitro activity:

Kinase Assay:

Cell Assay:

ln Vivo

Animal Protocol

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.

These protocols are for reference only. InvivoChem does not independently validate these methods.

Physicochemical Properties

Molecular Formula

C20H30O7

Molecular Weight

382.4480

Exact Mass

382.199

CAS #

56448-20-5

Related CAS #

56448-20-5

PubChem CID

11143436

Appearance

Typically exists as solid at room temperature

LogP

3.344

Hydrogen Bond Donor Count

Hydrogen Bond Acceptor Count

Rotatable Bond Count

Heavy Atom Count

Complexity

538

Defined Atom Stereocenter Count

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|

InChi Key

CAOCHWFVLJETKN-SADTYBKJSA-N

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

Chemical Name

4-[[(3E,6S,16R)-16-methyl-2,5-dioxo-1-oxacyclohexadec-3-en-6-yl]oxy]-4-oxobutanoic acid

Synonyms

A 26771B; A-26771B; A26771B

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

Shipping Condition

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Solubility Data

Solubility (In Vitro)

DMSO:

Water:

Ethanol:

Solubility (In Vivo)

(Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		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.

Calculator

Mass

Concentration

Volume

Molecular Weight*

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

Calculate the Mass of a compound required to prepare a solution of known volume and concentration
Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume

See Example

An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?

Enter 350.26 in the Molecular Weight (MW) box
Enter 10 in the Concentration box and choose the correct unit (mM)
Enter 5 in the Volume box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Concentration (Start)

Volume (Start)

Concentration (End)

Volume (End)

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:

Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
Enter 25 into the Concentration (End) box and select the correct unit (mM)
Enter 25 into the Volume (End) box and choose the correct unit (mL)
Click the “Calculate” button
The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box

Molecular formula

Total molecular weight

g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4 c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:

To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.

Definitions of molecular mass, molecular weight, molar mass and molar weight:

Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.

Volume (to add to vial)

Mass (in vial)

Desired Reconstitution Concentration

Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
Click the “Calculate” button
The answer appears in the Volume (to add to vial) box

In vivo Formulation Calculator (Clear solution)

Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)

Dosage mg/kg

Average weight of animals g

Dosing volume per animal μL

Number of animals

Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)

% DMSO

% Tween 80

% ddH₂O

Calculation results

Working concentration： mg/mL；

Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH₂O，mix and clarify.

Note： (1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.

Biological Data

X-ray crystal structure of berkeleylactone A (1).J Nat Prod.2017 Apr 28;80(4):1150-1160.
The extension inhibition assay allows the direct monitoring of the formation of stalled ribosome complexes (SRCs) on mRNA.J Nat Prod.2017 Apr 28;80(4):1150-1160.

A 26771B

Cell-free translation of GFP protein compared the effects of berkeleylactone A (1) and three known macrolide antibiotics—erythromycin, josamycin, and tylosin—on protein synthesis.J Nat Prod.2017 Apr 28;80(4):1150-1160.