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
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
| Molecular Formula | C45H57N3O9 |
| Molecular Weight | 783.9488 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 6 / 6 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23877026
https://www.ncbi.nlm.nih.gov/pubmed/25178661
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/23877026
https://www.ncbi.nlm.nih.gov/pubmed/25178661
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL267 |
|||
Target ID: CHEMBL394 |
2.4 µM [EC50] | ||
Target ID: CHEMBL395 |
3.6 µM [EC50] | ||
Target ID: CHEMBL220 |
3.09 µM [IC50] | ||
Target ID: CHEMBL387 |
2.02 µM [IC50] | ||
Target ID: CHEMBL392 |
0.82 µM [IC50] | ||
Target ID: CHEMBL352 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Curative | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| The mycotoxin beauvericin induces apoptotic cell death in H4IIE hepatoma cells accompanied by an inhibition of NF-κB-activity and modulation of MAP-kinases. | 2014-11-18 |
|
| Disturbance of antioxidant capacity produced by beauvericin in CHO-K1 cells. | 2014-05-02 |
|
| Verrucisidinol and verrucosidinol acetate, two pyrone-type polyketides isolated from a marine derived fungus, Penicillium aurantiogriseum. | 2010-11-01 |
|
| Production and migration of mycotoxins in sweet pepper analyzed by Multimycotoxin LC-MS/MS. | 2010-10-13 |
|
| Evaluation of beauvericin genotoxicity with the chromosomal aberrations, sister-chromatid exchanges and micronucleus assays. | 2010-10 |
|
| Mycotoxin production of selected Fusarium species at different culture conditions. | 2010-09-30 |
|
| The Fusarium mycotoxins enniatins and beauvericin cause mitochondrial dysfunction by affecting the mitochondrial volume regulation, oxidative phosphorylation and ion homeostasis. | 2010-09-30 |
|
| Antibacterial effect of the bioactive compound beauvericin produced by Fusarium proliferatum on solid medium of wheat. | 2010-09-01 |
|
| Antineoplastic activities of MT81 and its structural analogue in Ehrlich ascites carcinoma-bearing Swiss Albino mice. | 2010-08-19 |
|
| Beauvericin and ochratoxin A genotoxicity evaluated using the alkaline comet assay: single and combined genotoxic action. | 2010-08 |
|
| «Suspects» in etiology of endemic nephropathy: aristolochic acid versus mycotoxins. | 2010-06 |
|
| Nematicidal activity of beauvericin produced by the fungus Fusarium bulbicola. | 2010-05-18 |
|
| Beauvericin from the endophytic fungus, Fusarium redolens, isolated from Dioscorea zingiberensis and its antibacterial activity. | 2010-05 |
|
| Formation of fumonisins and other secondary metabolites by Fusarium oxysporum and F. proliferatum: a comparative study. | 2010-05 |
|
| Identification, mycotoxin risk and pathogenicity of Fusarium species associated with fig endosepsis in Apulia, Italy. | 2010-05 |
|
| Contamination by moulds of grape berries in Slovakia. | 2010-05 |
|
| Further data on the presence of Fusarium emerging mycotoxins enniatins, fusaproliferin and beauvericin in cereals available on the Spanish markets. | 2010-05 |
|
| Trichothecene and beauvericin mycotoxin production and genetic variability in Fusarium poae isolated from wheat kernels from northern Italy. | 2010-05 |
|
| Real and perceived risks for mycotoxin contamination in foods and feeds: challenges for food safety control. | 2010-04 |
|
| Oligonucleotide microarray for the identification of potential mycotoxigenic fungi. | 2010-03-23 |
|
| Beauvericin and enniatins H, I and MK1688 are new potent inhibitors of human immunodeficiency virus type-1 integrase. | 2009-12 |
|
| A beauvericin hot spot in the genus Isaria. | 2009-12 |
|
| Reactive oxygen species induced by beauvericin, patulin and zearalenone in CHO-K1 cells. | 2009-12 |
|
| Cytotoxic and antibacterial activities of endophytic fungi isolated from plants at the National Park, Pahang, Malaysia. | 2009-11-21 |
|
| Overview of analytical methods for beauvericin and fusaproliferin in food matrices. | 2009-11 |
|
| The nuclear protein Sge1 of Fusarium oxysporum is required for parasitic growth. | 2009-10 |
|
| Oxidative stress and DNA interactions are not involved in Enniatin- and Beauvericin-mediated apoptosis induction. | 2009-09 |
|
| Beauvericin decreases cell viability of wheat. | 2009-08 |
|
| Interactions between ABC-transport proteins and the secondary Fusarium metabolites enniatin and beauvericin. | 2009-07 |
|
| LC-MS/MS multi-analyte method for mycotoxin determination in food supplements. | 2009-06 |
|
| An inhibition study of beauvericin on human and rat cytochrome P450 enzymes and its pharmacokinetics in rats. | 2009-06 |
|
| Biosynthesis of the cyclooligomer depsipeptide bassianolide, an insecticidal virulence factor of Beauveria bassiana. | 2009-05 |
|
| Structural analysis of enniatin H, I, and MK1688 and beauvericin by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and their production by Fusarium oxysporum KFCC 11363P. | 2009-04 |
|
| Dominance of Group 2 and fusaproliferin production by Fusarium subglutinans from Iowa maize. | 2009-03 |
|
| Combinatorial mutasynthesis of scrambled beauvericins, cyclooligomer depsipeptide cell migration inhibitors from Beauveria bassiana. | 2009-01-26 |
|
| An overview of conventional and emerging analytical methods for the determination of mycotoxins. | 2009-01 |
|
| Development of a multi-mycotoxin liquid chromatography/tandem mass spectrometry method for sweet pepper analysis. | 2009-01 |
|
| Development of a LC-MS/MS method for the analysis of enniatins and beauvericin in whole fresh and ensiled maize. | 2008-11-12 |
|
| Cryptic subspecies and beauvericin production by Fusarium subglutinans from Europe. | 2008-10-31 |
|
| Biosynthesis of the cyclooligomer depsipeptide beauvericin, a virulence factor of the entomopathogenic fungus Beauveria bassiana. | 2008-09-22 |
|
| Cytotoxicities of enniatins H, I, and MK1688 from Fusarium oxysporum KFCC 11363P. | 2008-06-01 |
|
| Complex etiology, prophylaxis and hygiene control in mycotoxic nephropathies in farm animals and humans. | 2008-04 |
|
| Cytotoxicity and apoptosis induced by fumonisin B(1), beauvericin and ochratoxin A in porcine kidney PK15 cells: effects of individual and combined treatment. | 2008-04 |
|
| Diversity in Beauvericin and Enniatins H, I, and MK1688 by Fusarium oxysporum isolated from potato. | 2008-03-20 |
|
| Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. | 2008-01 |
|
| Statistical optimization of growth medium for the production of the entomopathogenic and phytotoxic cyclic depsipeptide beauvericin from Fusarium oxysporum KFCC 11363P. | 2008-01 |
|
| Fusarium avenaceum -- the North European situation. | 2007-10-20 |
|
| Further data on the production of beauvericin, enniatins and fusaproliferin and toxicity to Artemia salina by Fusarium species of Gibberella fujikuroi species complex. | 2007-09-15 |
|
| Cytotoxic and Antihaptotactic beauvericin analogues from precursor-directed biosynthesis with the insect pathogen Beauveria bassiana ATCC 7159. | 2007-09 |
|
| Supercritical fluid extraction of Beauvericin from maize. | 2004-02-27 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 21:11:55 GMT 2025
by
admin
on
Mon Mar 31 21:11:55 GMT 2025
|
| Record UNII |
26S048LS2R
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Preferred Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C1976
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
3000
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
PRIMARY | |||
|
DTXSID00891834
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
PRIMARY | |||
|
26048-05-5
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
PRIMARY | |||
|
3007984
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
PRIMARY | |||
|
C004456
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
PRIMARY | |||
|
26S048LS2R
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
PRIMARY | |||
|
C1011
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
PRIMARY | |||
|
BEAUVERICIN
Created by
admin on Mon Mar 31 21:11:55 GMT 2025 , Edited by admin on Mon Mar 31 21:11:55 GMT 2025
|
PRIMARY |