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Aureobasidin A

CAT: 0804-HY-P1975-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-P1975-01Size:1 mg
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Description
Aureobasidin A (Basifungin) is a cyclic peptide antibiotic with oral activity. Aureobasidin A is an inhibitor of inositol phosphorylated ceramide synthetase AUR1. Aureobasidin A has antifungal and antiparasitic activity[1][2][3].
CAS Number
127785-64-2
Product Name Alternative
Basifungin
UNSPSC
12352209
Target
Antibiotic; Fungal; Parasite
Type
Peptides
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/aureobasidin-a.html
Purity
99.31
Solubility
DMSO : 50 mg/mL (ultrasonic)
Smiles
O=C([C@@H](N(C([C@@H](NC([C@@H](N(C([C@@](OC1=O)([H])[C@H](C)CC)=O)C)C(C)C)=O)CC2=CC=CC=C2)=O)C)CC3=CC=CC=C3)N(CCC4)[C@]4([H])C(N[C@@](C(N([C@H](C(N[C@H](C(N([C@H]1C(C)(O)C)C)=O)CC(C)C)=O)C(C)C)C)=O)([H])[C@H](C)CC)=O
Molecular Formula
C60H92N8O11
Molecular Weight
1101.42
References & Citations
[1]Zheng L, et al. Chromosome 1 trisomy confers resistance to aureobasidin A in Candida albicans. Front Microbiol. 2023 Mar 17;14:1128160.|[2]Alqaisi AQI, et al. The antifungal Aureobasidin A and an analogue are active against the protozoan parasite Toxoplasma gondii but do not inhibit sphingolipid biosynthesis. Parasitology. 2018 Feb;145 (2) :148-155.|[3]Takesako K, et al. Biological properties of aureobasidin A, a cyclic depsipeptide antifungal antibiotic. J Antibiot (Tokyo) . 1993 Sep;46 (9) :1414-20.
Shipping Conditions
Blue Ice
Storage Conditions
-80°C, 2 years; -20°C, 1 year (Powder, sealed storage, away from moisture and light)
Scientific Category
Peptides
Clinical Information
No Development Reported

Chemical Information

Basifungin

Basifungin, also known as aureuobacidin A, is a phosphorylceramide synthase inhibitor,.

CAS Number127785-64-2
PubChem CID9919816
IUPAC Name(3S,6S,9S,12R,15S,18S,21S,24S,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
Molecular FormulaC60H92N8O11
Molecular Weight1101.4
XLogP8.5
Topological Polar Surface Area235
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count11
Rotatable Bond Count13
Heavy Atom Count79
Formal Charge0
Complexity2110
SMILES
CC[C@@H](C)[C@H]1C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N2CCC[C@H]2C(=O)N1)CC3=CC=CC=C3)C)CC4=CC=CC=C4)C(C)C)C)[C@H](C)CC)C(C)(C)O)C)CC(C)C)C(C)C)C
InChI
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
InChIKey
RLMLFADXHJLPSQ-QKCBWMAHSA-N
Chemical Structure
2D Structure
2D structure of Basifungin
CAS: 127785-64-2
CID: 9919816
Formula: C60H92N8O11
MW: 1101.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1101.4
XLogP38.5
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count11
Rotatable Bond Count13
Exact Mass1100.68855578
Monoisotopic Mass1100.68855578
Topological Polar Surface Area235 Ų
Heavy Atom Count79
Formal Charge0
Complexity2110
Isotope Atom Count0
Defined Atom Stereocenter Count11
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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C060208Aureobasidin A
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