Aureobasidin A

Aureobasidin A is a cyclic depsipeptide that has been found in A. pullulans and has diverse biological activities. It inhibits inositol phosphorylceramide synthase, an enzyme involved in sphingolipid biosynthesis (Kis = 0.18 and 0.23 for the C. albicans and S. cerevisiae enzymes, respectively). Aureobasidin A also inhibits P-glycoprotein (P-gp), also known as multidrug resistance protein 1 (MDR1, IC50 = 2.27 µM). It is active against various mammalian pathogenic fungi, including Candida and Cryptococcus (MICs = S. cerevisiae (MIC = 0.4 µg/ml). Aureobasidin A (80 mg/kg, p.o.) increases survival in a mouse model of candidiasis induced by C. albicans.Formal Name: cyclo[L-alloisoleucyl-N-methyl-L-valyl-L-leucyl-N,3-dimethyl-L-threonyl-(2R,3R)-2-hydroxy-3-methylpentanoyl-N-methyl-L-valyl-L-phenylalanyl-N-methyl-L-phenylalanyl-L-prolyl]. CAS Number: 127785-64-2. Synonyms: Antibiotic R 106I, Basifungin, LY295337, NK 204, R 106-1. Molecular Formula: C60H92N8O11. Formula Weight: 1101.4. Purity: >95%. Formulation: (Request formulation change), A solid. Solubility: Methanol: Soluble. SMILES: [H][C@@]12CCCN1C([C@@H](N(C([C@@H](NC([C@@H](N(C([C@@]([C@@H](CC)C)(OC([C@@H](N(C([C@@H](NC([C@@H](N(C([C@@]([H])(NC2=O)[C@H](C)CC)=O)C)C(C)C)=O)CC(C)C)=O)C)C(C)(C)O)=O)[H])=O)C)C(C)C)=O)CC3=CC=CC=C3)=O)C)CC4=CC=CC=C4)=O. InChi Code: InChI=1S/C60H92N8O11/c1-17-38(9)46-57(75)65(14)47(36(5)6)52(70)61-42(32-35(3)4)55(73)67(16)50(60(11,12)78)59(77)79-49(39(10)18-2)58(76)66(15)48(37(7)8)53(71)62-43(33-40-26-21-19-22-27-40)54(72)64(13)45(34-41-28-23-20-24-29-41)56(74)68-31-25-30-44(68)51(69)63-46/h19-24,26-29,35-39,42-50,78H,17-18,25,30-34H2,1-16H3,(H,61,70)(H,62,71)(H,63,69)/t38-,39-,42+,43+,44+,45+,46+,47+,48+,49-,50-/m1/s1. InChi Key: RLMLFADXHJLPSQ-QKCBWMAHSA-N. Origin: Synthetic, originally from Aureobasidium pullulans.