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Record Information
Version2.0
Creation Date2010-05-06 21:03:09 UTC
Update Date2014-12-24 20:26:28 UTC
Accession NumberT3D3740
Identification
Common NameBeauvericin
ClassSmall Molecule
DescriptionBeauvericin is a mycotoxin with antibiotic and insecticidal effects. 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. (7)
Compound Type
  • Amide
  • Amine
  • Fungal Toxin
  • Mycotoxin
  • Natural Compound
  • Organic Compound
  • Protein
Chemical Structure
Thumb
Synonyms
Synonym
1,7,13-Trioxa-4,10,16-triazacyclooctadecane, cyclic peptide deriv.
Cyclo(D-.alpha.-hydroxyisovaleryl-N-methyl-L-phenylalanyl-D-.alpha.-hydroxyisovaleryl-N-methyl-L-phenylalanyl-D-.alpha.-hydroxyisovaleryl-N-methyl-L-phenylalanyl)
cyclo(D-alpha-Hydroxyisovaleryl-L-N-methyl-Phe)3
Chemical FormulaC45H57N3O9
Average Molecular Mass783.949 g/mol
Monoisotopic Mass783.409 g/mol
CAS Registry Number26048-05-5
IUPAC Name(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
Traditional Namebeauvericin
SMILESCC(C)[C@H]1OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](OC(=O)[C@H](CC2=CC=CC=C2)N(C)C(=O)[C@H](OC(=O)[C@H](CC2=CC=CC=C2)N(C)C1=O)C(C)C)C(C)C
InChI IdentifierInChI=1/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+/s2
InChI KeyInChIKey=GYSCAQFHASJXRS-JTPGOKIJNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as cyclic depsipeptides. These are natural or synthetic compounds having sequences of amino and hydroxy carboxylic acid residues (usually α-amino and α-hydroxy acids) connected in a ring. The residues are commonly but not necessarily regularly alternating.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassDepsipeptides
Direct ParentCyclic depsipeptides
Alternative Parents
Substituents
  • Cyclic depsipeptide
  • Macrolide lactam
  • Alpha-amino acid ester
  • Macrolactam
  • Macrolide
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • Monocyclic benzene moiety
  • Benzenoid
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid ester
  • Lactam
  • Lactone
  • Carboxylic acid derivative
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceClear solution.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility>10 mg/mL
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00088 g/LALOGPS
logP5.25ALOGPS
logP7.27ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.8ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area139.83 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity213.47 m³·mol⁻¹ChemAxon
Polarizability83.04 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001l-4013002900-c6c232d3f69c9a9a1c08JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-7593320000-4ce9355a4c694e81cc4fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-5192020000-dd85d65bcace294f3c00JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-9020030000-258575fb2966c013816dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052f-1390162100-3faf3bba6a97dde28f8aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-5491302000-04a3f48a727cfed379bbJSpectraViewer
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (6)
Mechanism of ToxicityBeauvericin is cytotoxic and increases ion permeability in cell membranes by forming complexes with essential cations (Ca2+, Na+, K+) and by forming cation-selective channels in lipid membranes. This may affect ionic homeostasis, increasing the intracellular calcium concentration, and lead to apoptosis. Beauvericin is also genotoxic and causes DNA damage, either by directly forming DNA adducts, through increased intracellular calcium levels influencing endonuclease activity, or through oxidative stress. Beauvericin induces lipid peroxidation and production of reactive oxygen species, producing cytotoxic effects and immunosuppressive activity. In addition, beauvericin is a potent inhibitor of the acyl-CoA:cholesterol acyltransferase (ACAT), which plays an important role in cholesterol ester accumulation in atherogenesis and in cholesterol absorption from the intestine. In isolated terminal ilea and heart muscles of guinea pig, beauvericin decreases the contractility, shortening the action potential duration and depolarizing the membrane resting potential. Beauvericin is also known to inhibit certain cytochrome P-450 enzymes. (1, 2, 3, 4, 5)
MetabolismFree toxin may be removed by opsonization via the reticuloendothelial system (primarily the liver and kidneys) or it may be degraded through cellular internalization via the lysosomes. Lysosomes are membrane-enclosed organelles that contain an array of digestive enzymes, including several proteases.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not listed by IARC.
Uses/SourcesBeauvericin is a mycotoxin with antibiotic and insecticidal effects. 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. (7)
Minimum Risk LevelNot Available
Health EffectsBeauvericin is cytotoxic and immunosuppressive. It is also genotoxic and may thus be carcinogenic. (1)
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID105014
ChEMBL IDCHEMBL1977672
ChemSpider ID2277520
KEGG IDC11590
UniProt IDNot Available
OMIM ID
ChEBI ID3000
BioCyc IDNot Available
CTD IDNot Available
Stitch IDBeauvericin
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkBeauvericin
References
Synthesis ReferenceNot Available
MSDST3D3740.pdf
General References
  1. Klaric MS, Darabos D, Rozgaj R, Kasuba V, Pepeljnjak S: Beauvericin and ochratoxin A genotoxicity evaluated using the alkaline comet assay: single and combined genotoxic action. Arch Toxicol. 2010 Aug;84(8):641-50. doi: 10.1007/s00204-010-0535-7. Epub 2010 Mar 30. [20352195 ]
  2. Ferrer E, Juan-Garcia A, Font G, Ruiz MJ: Reactive oxygen species induced by beauvericin, patulin and zearalenone in CHO-K1 cells. Toxicol In Vitro. 2009 Dec;23(8):1504-9. doi: 10.1016/j.tiv.2009.07.009. Epub 2009 Jul 23. [19596061 ]
  3. Kouri K, Lemmens M, Lemmens-Gruber R: Beauvericin-induced channels in ventricular myocytes and liposomes. Biochim Biophys Acta. 2003 Jan 31;1609(2):203-10. [12543382 ]
  4. Mei L, Zhang L, Dai R: An inhibition study of beauvericin on human and rat cytochrome P450 enzymes and its pharmacokinetics in rats. J Enzyme Inhib Med Chem. 2009 Jun;24(3):753-62. doi: 10.1080/14756360802362041. [18956271 ]
  5. Jestoi M: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008 Jan;48(1):21-49. doi: 10.1080/10408390601062021. [18274964 ]
  6. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  7. Wikipedia. Beauvericin. Last Updated 12 January 2010. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Sterol o-acyltransferase activity
Specific Function:
Catalyzes the formation of fatty acid-cholesterol esters, which are less soluble in membranes than cholesterol. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:
SOAT1
Uniprot ID:
P35610
Molecular Weight:
64733.975 Da
References
  1. Tomoda H, Huang XH, Cao J, Nishida H, Nagao R, Okuda S, Tanaka H, Omura S, Arai H, Inoue K: Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J Antibiot (Tokyo). 1992 Oct;45(10):1626-32. [1473990 ]
2. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Klaric MS, Darabos D, Rozgaj R, Kasuba V, Pepeljnjak S: Beauvericin and ochratoxin A genotoxicity evaluated using the alkaline comet assay: single and combined genotoxic action. Arch Toxicol. 2010 Aug;84(8):641-50. doi: 10.1007/s00204-010-0535-7. Epub 2010 Mar 30. [20352195 ]
  2. Jestoi M: Emerging fusarium-mycotoxins fusaproliferin, beauvericin, enniatins, and moniliformin: a review. Crit Rev Food Sci Nutr. 2008 Jan;48(1):21-49. doi: 10.1080/10408390601062021. [18274964 ]
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase. May provide cholesteryl esters for lipoprotein secretion from hepatocytes and intestinal mucosa.
Gene Name:
SOAT2
Uniprot ID:
O75908
Molecular Weight:
59895.735 Da
References
  1. Tomoda H, Huang XH, Cao J, Nishida H, Nagao R, Okuda S, Tanaka H, Omura S, Arai H, Inoue K: Inhibition of acyl-CoA: cholesterol acyltransferase activity by cyclodepsipeptide antibiotics. J Antibiot (Tokyo). 1992 Oct;45(10):1626-32. [1473990 ]