Basic information
- CAS
127785-64-2- Standard SMILES
CC[C@@H](C)[C@@H]1OC(=O)[C@H](C(C)(C)O)N(C)C(=O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)N(C)C(=O)[C@@H]([C@H](C)CC)NC(=O)[C@@H]2CCCN2C(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@H](Cc2ccccc2)NC(=O)[C@H](C(C)C)N(C)C1=O- InChIKey
RLMLFADXHJLPSQ-NPPFTVEMSA-N- Molecular formula
- C60H92N8O11
- Average molar mass
- 1,101.4 g/mol
- Monoisotopic mass
- 1,100.68855578
Overview
Basifungin has been reported in Aureobasidium pullulans with data available.
Names & identifiers
- Preferred name
- Aureobasidin-A
- IUPAC
- (3S,6S,9S,12S,15S,18S,21S,24R,27S)-3,6-dibenzyl-12,24-bis[(2R)-butan-2-yl]-15-(2-hydroxypropan-2-yl)-4,10,16,22-tetramethyl-18-(2-methylpropyl)-9,21-di(propan-2-yl)-13-oxa-1,4,7,10,16,19,22,25-octazabicyclo[25.3.0]triacontane-2,5,8,11,14,17,20,23,26-nonone
- English name
- Basifungin
- Molecular formula
- C60H92N8O11
- Molecular weight
- 1101.42
Names & synonyms
Aureobasidin-ASCHEMBL30758653F90311(2R,3R)-Hmp-MeVal-Phe-MePhe-Pro-alle-MeVal-Leucine-betaHOMeVal(2R,3R)2-Hydroxy-3-methylpentanoic acid-N-methylvaline-Phenylalanine-N-methylphenylalanine-Proline-alloisoleucine-Methylvaline-Leucine-betahydroxy-N-methylvalineaureobasidin ALY-295337BasifunginBrazil FenjingBasifungin(AbA)Jin Basidiomycin AAureobasidin A (AbA)
Show more names
Aureobasidin A (9CI)Basifungin/Aureobasidin AAureobasidin A(Basifungin)
Database identifiers
- CAS
127785-64-2- PubChem CID
- 72050
Properties
Computed structural properties
- XLogP
- 8.5
- Topological polar surface area
- 235 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 13
- Heavy atoms
- 79
- Formal charge
- 0
- Complexity
- 2,110
Physicochemical properties
- Boiling point
- 1229.1 · 1229.1±65.0 °C(Predicted)
- Density
- 1.19 · 1.19±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C, · Store at -20°C, protect from light
- solubility
- 100 mg/mL · DMSO : 100 mg/mL (90.79 mM; Need ultrasonic)
- pka
- 13.35 · 13.35±0.70(Predicted)
- form
- Solid
- color
- White to off-white
- InChIKey
- RLMLFADXHJLPSQ-UBDQFPLBNA-N
- FDA UNII
- 0 USO6I6U · VV0USO6I6U
Chemistry & industry
Applications
DescriptionAureobasidin A (R-106; Basifungin), the lead compound, has potent activity in vitro against many clinically relevant fungi, including Candida spp. , Cryptococcus neoformans, Blastomyces dermatidis, Histoplasma capsulatum, and some Aspergillus species. In vivo, in a murine model of systemic candidiasis, the compound was well tolerated and more effective than AmB and fluconazole. Molecular studies of aureobasidin A-resistant mutants of S. cerevisiae have led to the discovery of the aureobasidin resistance (AUR1) gene. It has been suggested that the gene product of the wild-type AUR1+ is the molecular target for aureobasidin A. AUR1+ can fully restore the activity of IPC synthase and sphingolipid synthesis, and that aureobasidin A does indeed function as a potent inhibitor of IPC synthase. The inhibition of this essential biosynthetic step leads to ceramide accumulation in growing cells and cell death. Cytological studies in S. cerevisiae after aureobasidin A exposure and after disruption of the AUR1+ gene suggest that the ultimate effect of the compound is the destruction of the cell membrane and the disturbance of intracellular microtubule organization[2].
UsesBasifungin, also known as aureuobacidin A, 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.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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