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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H57N3O9
Molecular Weight 783.9488
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEAUVERICIN

SMILES

CC(C)[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](OC(=O)[C@H](CC3=CC=CC=C3)N(C)C(=O)[C@H](OC(=O)[C@H](CC4=CC=CC=C4)N(C)C1=O)C(C)C)C(C)C

InChI

InChIKey=GYSCAQFHASJXRS-FFCOJMSVSA-N
InChI=1S/C45H57N3O9/c1-28(2)37-40(49)46(7)35(26-32-21-15-11-16-22-32)44(53)56-39(30(5)6)42(51)48(9)36(27-33-23-17-12-18-24-33)45(54)57-38(29(3)4)41(50)47(8)34(43(52)55-37)25-31-19-13-10-14-20-31/h10-24,28-30,34-39H,25-27H2,1-9H3/t34-,35-,36-,37+,38+,39+/m0/s1

HIDE SMILES / InChI

Molecular Formula C45H57N3O9
Molecular Weight 783.9488
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Beauvericin is a famous mycotoxin produced by many fungi, such as Beaveria bassiana and Fusarium spp. Beauvericin is a cyclic hexadepsipeptide (Figure 1) that belongs to the enniatin antibiotic family. It contains three D-hydroxyisovaleryl and three N-methylphenylalanyl residues in an alternating sequence. Beauvericin was first isolated from Beaveria bassiana, which is a common and commercial entomopathogenic mycoinsecticide. Beauvericin was one of the active constituents of B. bassiana and was confirmed to have antimicrobial and anti-tumor activities. Beauvericin has a strong antibacterial activity against human, animal and plant pathogenic bacteria with no selectively between Gram-positive and Gram-negative bacteria. The cytotoxicity of beauvericin to human tumor cells has been frequently reported.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.4 µM [EC50]
3.6 µM [EC50]
3.09 µM [IC50]
2.02 µM [IC50]
0.82 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Curative
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
0.2 mg/kg
Route of Administration: Oral
In Vitro Use Guide
Incubation of H4IIE cells with beauvericin (10uM, 2 h) strongly diminished phosphorylation of the MAP kinase ERK (p44/p42) as a prerequisite of MAPK activation
Substance Class Chemical
Record UNII
26S048LS2R
Record Status Validated (UNII)
Record Version