Physicochemical Properties
| Molecular Formula | C60H92N8O12 |
| Molecular Weight | 1117.44 |
| Exact Mass | 1100.69 |
| Elemental Analysis | C, 64.49; H, 8.30; N, 10.03; O, 17.18 |
| CAS # | 127785-64-2 |
| Related CAS # | 127785-64-2; |
| PubChem CID | 9919816 |
| Appearance | White to off-white solid powder |
| Density | 1.19g/cm3 |
| Boiling Point | 1229.1ºC at 760 mmHg |
| Flash Point | 697.1ºC |
| Vapour Pressure | 0mmHg at 25°C |
| Index of Refraction | 1.574 |
| LogP | 4.889 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 11 |
| Rotatable Bond Count | 13 |
| Heavy Atom Count | 79 |
| Complexity | 2110 |
| Defined Atom Stereocenter Count | 11 |
| SMILES | O=C1[C@]2([H])C([H])([H])C([H])([H])C([H])([H])N2C([C@]([H])(C([H])([H])C2C([H])=C([H])C([H])=C([H])C=2[H])N(C([H])([H])[H])C([C@]([H])(C([H])([H])C2C([H])=C([H])C([H])=C([H])C=2[H])N([H])C([C@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])N(C([H])([H])[H])C([C@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])OC([C@]([H])(C(C([H])([H])[H])(C([H])([H])[H])O[H])N(C([H])([H])[H])C([C@]([H])(C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H])N([H])C([C@]([H])(C([H])(C([H])([H])[H])C([H])([H])[H])N(C([H])([H])[H])C([C@@]([H])([C@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])N1[H])=O)=O)=O)=O)=O)=O)=O)=O |
| InChi Key | BGBIMGBOAIOSPU-PHHQQPDVSA-N InChi Code |
| InChi Code | InChI=1S/C60H92N8O12/c1-17-38(9)46(56(76)65(14)47(36(5)6)51(71)61-42(32-35(3)4)54(74)67(16)60(58(78)80-60)59(11,12)79)63-50(70)44-30-25-31-68(44)55(75)45(34-41-28-23-20-24-29-41)64(13)53(73)43(33-40-26-21-19-22-27-40)62-52(72)48(37(7)8)66(15)57(77)49(69)39(10)18-2/h19-24,26-29,35-39,42-49,69,79H,17-18,25,30-34H2,1-16H3,(H,61,71)(H,62,72)(H,63,70)/t38-,39?,42+,43+,44+,45+,46+,47+,48+,49?,60+/m1/s1 |
| Chemical Name | Valine, 3-hydroxy-N-(N-(N-(N-(1-(N-(N-(N-(2-hydroxy-3-methyl-1-oxopentyl)-N-methylvalyl)phenylalanyl)-N-methylphenylalanyl)prolyl)alloisoleucyl)-N-methylvalyl)leucyl)-N-methyl-, alpha-1-lactone |
| Synonyms | Aureobasidin A; LY 295337; LY295337; NK 204 R106-1 |
| 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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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
| ln Vitro | Aureobasidin A stops the growth of yeast cells by depriving them of vital inositolphosphorylceramides and intoxicating them with ceramides[2]. |
| References |
[1]. Structure of aureobasidin A. J Antibiot (Tokyo). 1991 Sep;44(9):925-33. [2]. Aureobasidin A arrests growth of yeast cells through both ceramide intoxication and deprivation of essential inositolphosphorylceramides. Mol Microbiol. 2009 Mar;71(6):1523-37. [3]. Aureobasidin A, an antifungal cyclic depsipeptide antibiotic, is a substrate for both human MDR1 and MDR2/P-glycoproteins. FEBS Lett. 1996 Dec 9;399(1-2):29-32. |
| Additional Infomation |
Basifungin, also known as aureuobacidin A, is a phosphorylceramide synthase inhibitor,. Aureobasidin A has been reported in Aureobasidium pullulans with data available. Basifungin is an orally available cyclic depsipeptide antibiotic produced by Aureobasidium pullulans that is a fungicide at low concentrations. Aureobasidin A inhibits inositol phosphorylceramide synthase, an enzyme that catalyzes a key step in fungal sphingolipid biosynthesis. This may inhibit fungal cell growth. |
Solubility Data
| Solubility (In Vitro) | DMSO : ~100 mg/mL (~90.79 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.27 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (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 25.0 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: ≥ 2.5 mg/mL (2.27 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. Solubility in Formulation 3: 10% DMSO+40% PEG300+5% Tween-80+45% Saline: ≥ 2.5 mg/mL (2.27 mM) (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 0.8949 mL | 4.4745 mL | 8.9490 mL | |
| 5 mM | 0.1790 mL | 0.8949 mL | 1.7898 mL | |
| 10 mM | 0.0895 mL | 0.4475 mL | 0.8949 mL |