Compound: Beauvericin
SMILES: O=C1O[C@@H](C(=O)N([C@H](C(=O)O[C@@H](C(=O)N([C@H](C(O[C@@H](C(N([C@H]1Cc2ccccc2)C)=O)C(C)C)=O)Cc3ccccc3)C)C(C)C)Cc4ccccc4)C)C(C)C
InChIKey: GYSCAQFHASJXRS-FFCOJMSVSA-N
Synonyms: Beauvericin, 26048-05-5, (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone, DTXSID00891834, 26S048LS2R, CHEBI:3000, RefChem:116825, DTXCID901031255, (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tris(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone, (3R,6S,9R,12S,15R,18S)-3,9,15-tribenzyl-4,10,16-trimethyl-6,12,18-tri(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone, (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexaone, (3S,6R,9S,12R,15S,18R)-3,9,15-tribenzyl-6,12,18-triisopropyl-4,10,16-trimethyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone, C45H57N3O9, MFCD30541349, UNII-26S048LS2R, GYSCAQFHASJXRS-FFCOJMSVSA-N, SCHEMBL29355, CHEMBL249052, orb1707579, MSK7258, HY-N6739, MSK7258-100A, AKOS030622850, CS-W020817, FB18149, NCGC00380798-01, NS00018333, A12357, Beauvericin Solution in Acetonitrile, 100ug/mL, Cyclo[(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy-3-methylbutanoyl-N-methyl-L-phenylalanyl-(2R)-2-hydroxy -3-methylbutanoyl-N-methyl-L-phenylalanyl]
Theoretical properties:
molecular_formula: C45H57N3O9
molecular_weight: 783.9 g/mol
exact_mass: 783.40948040 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 9
rotatable_bond_count: 9
heavy_atom_count: 57
topological_polar_surface_area: 140 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Beauvericin is a trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues. It has a role as an ionophore, a mycotoxin, an antineoplastic agent, an antifungal agent, an antibiotic insecticide, a P450 inhibitor, an apoptosis inhibitor and a fungal metabolite.
chebi: A trimeric cyclodepsipeptide composed from alternating methylphenylalanyl and hydroxyvaleryl residues.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Beauvericin is a depsipeptide with antibiotic and insecticidal effects belonging to the enniatin family. It was isolated from the fungus Beauveria bassiana, but is also produced by several other fungi, including several Fusarium species; it may therefore occur in grain (such as corn, wheat and barley) contaminated with these fungi. Beauvericin is active against Gram-positive bacteria and mycobacteria, and is also capable of inducing programmed cell death in mammals.
Chemically, beauvericin is a cyclic hexadepsipeptide with alternating N-methyl-phenylalanyl and D-hydroxy-iso-valeryl residues. Its ion-complexing capability allows beauvericin to transport alkaline earth metal and alkali metal ions across cell membranes.
Beauvericin has in vitro fungicidal effects on Candida parapsilosis when used in combination with the antifungal drug ketoconazole at dosages of 0.1 μg/ml.  Increased survivability rates and low cytotoxicity were also observed in mouse models.